Compound for organic electric element, organic electric element using the same, and an electronic device thereof

ABSTRACT

The present invention provides the compound Formula A, an organic electric element comprising a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, and electronic device thereof, and by comprising the compound of Formula A in the organic material layer, the driving voltage of the organic electric element can be lowered, and the luminous efficiency and life time of the organic electric element can be improved.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application is a Continuation-in-Part of U.S. patent application Ser. No. 17/309,586 filed Jun. 7, 2021, which is a national stage entry of International PCT Application No.: PCT/KR2019/015809, filed on Nov. 19, 2019, and claims priority from and the benefit under 35 U.S.C. § 119 to § 121, and § 365 of Korean Patent Application No. 10-2018-0156638, filed on Dec. 7, 2018 which is hereby incorporated by reference for all purposes as if fully set forth herein. Further, this application claims the benefit of priority in countries other than U.S., which is hereby incorporated by reference herein.

BACKGROUND Technical Field

The present invention relates to compounds for organic electric elements, organic electric elements comprising the same, and electronic devices thereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenon in which electric energy is converted into light energy of an organic material. An organic electric element utilizing the organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer interposed therebetween. In many cases, the organic material layer has a multi-layered structure having respectively different materials in order to improve efficiency and stability of an organic electric element, and for example, may comprise a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, or the like.

Materials used as an organic material layer in an organic electric element may be classified into a light emitting material and a charge transport material, for example, a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to its function. Further, the light emitting material may be divided into a high molecular weight type and a low molecular weight type according to its molecular weight, and may also be divided into a fluorescent material derived from excited singlet states of electron and a phosphorescent material derived from excited triplet states of electron according to its light emitting mechanism. Further, the light emitting material may be divided into blue, green, and red light emitting material and yellow and orange light emitting material required for better natural color reproduction according to its light emitting color.

Meanwhile, when only one material is used as a light emitting material, there occur problems of shift of a maximum luminescence wavelength to a longer wavelength due to intermolecular interactions and lowering of the efficiency of a corresponding element due to deterioration in color purity or a reduction in luminous efficiency. On account of this, a host/dopant system may be used as the light emitting material in order to enhance the color purity and increase the luminous efficiency through energy transfer. This is based on the principle that if a small amount of dopant having a smaller energy band gap than a host forming a light emitting layer is mixed in the light emitting layer, then excitons generated in the light emitting layer are transported to the dopant, thus emitting light with high efficiency. With regard to this, since the wavelength of the host is shifted to the wavelength band of the dopant, light having a desired wavelength can be obtained according the type of the dopant.

Currently, the power consumption is required more than more as size of display becomes larger and larger in the portable display market. Therefore, the power consumption is very important factor in the portable display with a limited power source of the battery, and efficiency and life span issues must also be solved.

Efficiency, life span, driving voltage, and the like are correlated with each other. If efficiency is increased, then driving voltage is relatively lowered, and the crystallization of an organic material due to Joule heating generated during operation is reduced as driving voltage is lowered. As a result, life span tends to increase. However, efficiency cannot be maximized only by simply improving the organic material layer. This is because long life span and high efficiency can be simultaneously achieved when an optimal combination of energy levels and T₁ values, inherent material properties (mobility, interfacial properties, etc.), and the like among the respective layers included in the organic material layer is given.

Therefore, there is a need to develop a light emitting material that has high thermal stability and can efficiently a charge balance in the light-emitting layer. That is, in order to allow an organic electric element to fully exhibit excellent features, it should be prerequisite to support a material constituting an organic material layer in the element, for example, a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, or the like, by a stable and efficient material. However, the stable and efficient material of organic material layer for an organic electronic element has not been fully developed yet, in particular, it is strongly required to develop host material of the light emitting layer.

Object, Technical Solution and Effects of the Invention

The present invention is to provide compound lowering a driving voltage, improving luminous efficiency and lifetime of the element, an organic electric element comprising the same, and an electronic device thereof.

In an aspect of the present invention, the present invention provides the compound represented by the following formula, organic electric elements comprising the same, and electronic devices thereof.

In another aspect of the present invention, the present invention provides an organic electric element comprising compound represented by Formula 1 and compound represented by Formula 2 in a light emitting layer, and an electronic device thereof.

In another aspect of the present invention, the present invention provides the compound of formula A, organic electric elements comprising the same, and electronic devices thereof.

By using the compound according to embodiment of the present invention, a driving voltage of element can be lowered and the luminous efficiency and lifetime of the element can be also significantly improved.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGS. 1 and 2 illustrate an example of an organic electroluminescent element according to the present invention: 100 and 200 are each an organic electric element, 110 is a substrate, 120 is a first electrode, 130 is a hole injection layer, 140 is a hole transport layer, 141 is a buffer layer, 150 is a light emitting layer, 151 is an emission-auxiliary layer, 160 is an electron transport layer, 170 is an electron injection layer, 180 is a second electrode, 190 is a layer for improving luminous efficiency, 230 is a first hole injection layer, 240 is a first hole transport layer, 250 is a first light emitting layer, 260 is a first electron transport layer, 330 is a second hole injection layer, 340 is a second hole transport layer, 350 is a second light emitting layer, 360 is a second electron transport layer, CGL is a charge generation layer, ST1 is a first stack and ST2 is a second stack.

DETAILED DESCRIPTION

Unless otherwise stated, the term “aryl group” or “arylene group” as used herein has, but not limited to, 6 to 60 carbon atoms. The aryl group or arylene group in the present invention may comprise a monocyclic ring, ring assemblies, a fused polycyclic system, spiro-compounds and the like. In addition, unless otherwise stated, a fluorenyl group may be comprised in an aryl group and a fluorenylene group may be comprised in an arylene group.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylene group” as used herein means univalent or bivalent functional group in which R, R′ and R″ are all hydrogen in the following structure, “substituted fluorenyl group” or “substituted fluorenylene group” means that at least any one of R, R′ and R″ is a substituent other than hydrogen, and the case where R and R′ are bonded to each other to form the spiro compound together with the carbon bonded to them is comprised.

The term “spiro-compound” as used herein has a spiro union which means union having one atom as the only common member of two rings. The common atom is designated as ‘spiro atom’. The compounds are defined as ‘monospiro-’, ‘dispiro-’ or ‘trispiro-’ depending on the number of spiro atoms in one compound.

The term “heterocyclic group” used in the specification comprises a non-aromatic ring as well as an aromatic ring like “heteroaryl group” or “heteroarylene group”. Unless otherwise stated, the term “heterocyclic group” means, but not limited to, a ring containing one or more heteroatoms and having 2 to 60 carbon atoms. Unless otherwise stated, the term “heteroatom” as used herein refers to N, O, S, P or Si and heterocyclic group means a monocyclic, ring assemblies, a fused polycyclic system or Spiro compound containing a heteroatom.

The term “heterocyclic group” used in the specification may comprise compound comprising a heteroatom group such as SO₂, P═O, etc., as the following compounds, instead of carbon forming a ring.

The term “aliphatic ring group” as used herein refers to a cyclic hydrocarbon except for aromatic hydrocarbons, and comprises a monocyclic ring, ring assemblies, a fused polycyclic system, spiro compounds, and the like, and unless otherwise specified, it means a ring of 3 to 60 carbon atoms, but not limited thereto. For example, a fused ring formed by benzene being an aromatic ring with cyclohexane being a non-aromatic ring corresponds to aliphatic ring group.

In this specification, a ‘group name’ corresponding to an aryl group, an arylene group, a heterocyclic group, and the like exemplified for each symbol and its substituent may be written in the name of functional group reflecting the valence, and may also be described as the name of a parent compound. For example, in the case of phenanthrene which is a kind of aryl group, it may be described by distinguishing valence such as ‘phenanthryl (group)’ when it is ‘monovalent group’, and ‘phenanthrylene (group)’ when it is ‘divalent group’, and regardless of its valence, it may also be described as ‘phenanthrene’ which is a parent compound name. Similarly, in the case of pyrimidine, it may be described as ‘pyrimidine’ regardless of its valence, and it may also be described as the name of corresponding functional group such as pyrimidinyl (group) when it is ‘monovalent group’, and ‘pyrimidinylene (group)’ when it is ‘divalent group’.

In addition, in the present specification, the numbers and alphabets indicating a position may be omitted when describing a compound name or a substituent name, For example, pyrido[4,3-d]pyrimidine, benzopuro[2,3-d]pyrimidine and 9,9-dimethyl-9H-fluorene can be described as pyridopyrimidine, benzofurropyrimidine and dimethylfluorene, respectively. Therefore, both benzo[g]quinoxaline and benzo[f]quinoxaline can be described as benzoquinoxaline.

In addition, unless otherwise expressed, where any formula of the present invention is represented by the following formula, the substituent according to the index may be defined as follows.

In the above formula, where a is an integer of zero, the substituent R¹ is absent, that is, hydrogen atoms are bonded to all the carbon constituting the benzene ring. Here, chemical formulas or compounds may be written described by omitting the indication of hydrogen bonded to carbon. In addition, one substituent R¹ is bonded to any carbon of the carbons forming the benzene ring when “a” is an integer of 1. Similarly, where “a” is an integer of 2 or 3, for example, as in the following formulas, substituents R¹s may be bonded to the carbon of the benzene ring. Also, where “a” is an integer of 4 to 6, substituents R¹s are bonded to the carbon of the benzene ring in a similar manner. Further, where “a” is an integer of 2 or more, R¹s may be the same or different from each other.

In addition, unless otherwise specified in the present specification, the ring formed by bonding between adjacent groups may be selected from the group consisting of a C₆-C₆₀ aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least one heteroatom selected from the group consisting of O, N, S, Si, and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring group and a combination thereof.

Hereinafter, a laminated structure of the organic electric element comprising the compound of the present invention will be described with reference to FIG. 1 .

In the following description of the present invention, a detailed description of known configurations and functions incorporated herein will be omitted when it may make the subject matter of the present invention rather unclear.

In addition, it will be understood that when an element such as a layer, film, region or substrate is referred to as being “on” or “over” another element, it can be directly on the other element or intervening elements may also be present. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

FIG. 1 illustrates an example of an organic electric element according to an embodiment of the present invention.

Referring to the FIG. 1 , an organic electric element 100 according to an embodiment of the present invention includes a first electrode 120 formed on a substrate 110, a second electrode 180, and an organic material layer formed between the first electrode 120 and the second electrode 180 and comprising the compound of the present invention. Here, the first electrode 120 may be an anode (positive electrode), and the second electrode 180 may be a cathode (negative electrode). In the case of an inverted organic electroluminescent element, the first electrode may be a cathode, and the second electrode may be an anode.

The organic material layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 stacked in sequence on the first electrode 120. Here, at least one layer of the organic material layer may be omitted, or a hole blocking layer, an electron blocking layer, an emission-auxiliary layer 151, an electron transport-auxiliary layer, a buffer layer 141, etc. may be further included in the organic material layer, and the electron transport layer 160 or the like may serve as a hole blocking layer.

In addition, according to another embodiment of the present invention, the organic material layer may be a form consisting of a plurality of stacks, wherein the stacks comprise a hole transport layer, a light emitting layer, and an electron transport layer, respectively. This will be described with reference to FIG. 2 .

Referring to FIG. 2 , two or more sets of stacks of the organic material layers ST1 and ST2 may be formed between the first electrode 120 and the second electrode 180 in the organic electric element 200 according to another embodiment of the present invention, wherein the organic material layers are consisted of multiple layers, respectively, and the charge generation layer CGL may be formed between the stacks of the organic material layer.

Specifically, the organic electric element according to an embodiment of the present invention may comprise a first electrode 120, a first stack ST1, a charge generation layer CGL, a second stack ST2, a second electrode 180 and a layer for improving light efficiency 190.

The first stack ST1 is an organic layer formed on the first electrode 120, and the first stack ST1 may comprise the first hole injection layer 230, the first hole transport layer 240, the first light emitting layer 250 and the first electron transport layer 260 and the second stack ST2 may comprise a second hole injection layer 330, a second hole transport layer 340, a second light emitting layer 350 and a second electron transport layer 360. As such, the first stack and the second stack may be the organic layers having the same or different stacked structures, and as described above, may further comprise an emission-auxiliary layer between the hole transport layers 240 and 340 and the light emitting layers 250 and 350, and an electron transport auxiliary layer between the light emitting layers 250 and 350 and the electron transport layers 260 and 360.

The charge generation layer CGL may be formed between the first stack ST1 and the second stack ST2. The charge generating layer CGL is formed between the first light emitting layer 240 and the second light emitting layer 340 to increase the current efficiency generated in each light emitting layer and to smoothly distribute charges.

In FIG. 2 , n may be an integer of 1 to 5 and the charge generation layer CGL and the third stack may be further stacked on the second stack ST2 when n is 2.

When a plurality of light emitting layers are formed in a multi-layer stack structure as shown in FIG. 2 , it is possible to manufacture an organic electroluminescent element that emits not only white light but also various colors, wherein the white light is emitted by the mixing effect of light emitted from each light emitting layer.

In addition, the organic electric element according to an embodiment of the present invention may further include a protective layer or a layer for improving luminous efficiency. The layer for improving luminous efficiency may be formed on one side of sides of the first electrode or one side of sides of the second electrode, wherein the one side is not facing the organic material layer. FIG. 2 shows an example in which the light efficiency improving layer 190 is formed on the second electrode.

The inventive compound employed in the organic material layer may be used as a material of a hole injection layer 130, 230 and 330, a hole transport layer 140, 240 and 340, an emission-auxiliary layer 151, an electron transport-auxiliary layer, an electron transport layer 160, 260 and 360 or an electron injection layer 170, as host or dopant of a light emitting layer 150, 250 and 350, or as a material of a layer for improving luminous efficiency 190. Preferably, compound of Formula 1, Formula 1-E or Formula A of the present invention or a mixture of compound of Formula 1, Formula 1-E or Formula A and compound of Formula 2, Formula G or Formula H can be used as host of a light emitting layer.

On the other hand, even if the core is same or similar, the band gap, the electrical characteristics, the interface characteristics and the like may be different depending on which substituent is bonded at which position. Therefore, there is a need to study the selection of the core and the combination of the core and the sub-substituent bonded to the core. In particular, long life span and high efficiency can be simultaneously achieved when the optimal combination of energy levels and T₁ values, inherent material properties (mobility, interfacial properties, etc.) and the like among the respective layers of an organic material layer is achieved.

Therefore, the energy level and T₁ value between the respective layers of the organic material layer, inherent material properties (mobility, interfacial properties, etc.) and the like can be optimized by using compound of Formula 1 or a mixture of compound of Formula 1 and compound of Formula 2 as host of a light emitting layer in the present invention.

The organic electric element according to an embodiment of the present invention may be manufactured using various deposition methods. The organic electric element according to an embodiment of the present invention may be manufactured using a PVD (physical vapor deposition) method or CVD (chemical vapor deposition) method. For example, the organic electric element may be manufactured by depositing a metal, a conductive metal oxide, or alloy on the substrate to form the anode 120, forming the organic material layer including the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, the electron transport layer 160, and the electron injection layer 170 thereon, and then depositing a material which can be used as the cathode 180, thereon. In addition, an emitting auxiliary layer 151 may be formed between a hole transport layer 140 and a light emitting layer 150, and an electron transport-auxiliary layer may be formed between a light emitting layer 150 and an electron transport layer 160.

In addition, the organic material layer may be manufactured in such a manner that a smaller number of layers are formed using various polymer materials by a soluble process or solvent process, for example, spin coating, nozzle printing, inkjet printing, slot coating, dip coating, roll-to-roll, doctor blading, screen printing, or thermal transfer, instead of deposition. Since the organic material layer according to the present invention may be formed in various ways, the scope of protection of the present invention is not limited by a method of forming the organic material layer.

The organic electric element according to an embodiment of the present invention may be of a top emission type, a bottom emission type, or a dual emission type depending on the material used.

In addition, the organic electric element according to the present invention may be selected from group consisting of an organic electroluminescent element, an organic solar cell, an organic photo conductor, an organic transistor, an element for monochromatic illumination and an element quantum dot display.

Another embodiment of the present invention provides an electronic device including a display device which includes the above described organic electric element, and a control unit for controlling the display device. Here, the electronic device may be a wired/wireless communication terminal which is currently used or will be used in the future, and covers all kinds of electronic devices including a mobile communication terminal such as a cellular phone, a personal digital assistant (PDA), an electric dictionary, a point-to-multipoint (PMP), a remote controller, a navigation unit, a game player, various kinds of TVs, various kinds of computers and so on.

Hereinafter, the compound according to an aspect of the present invention will be described.

Compound according to one aspect of the present invention may be represented by Formula 1.

In formula 1, each of symbols may be defined as follows.

X₁ is O or S.

Ar¹ and Ar² are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group.

Where Ar¹ and Ar² are each an aryl group, the aryl group may be preferably a C₆-C₃₀ aryl group, more preferably a C₆-C₁₈ aryl group, for example, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene, pyrene, triphenylene, and the like. Where Ar¹ and Ar² are each a heterocyclic group, the heterocyclic group may be preferably a C₂-C₃₀ heterocyclic group, more preferably a C₂-C₁₈ heterocyclic group, for example, pyridine, quinoline, isoquinoline, carbazole, phenylcarbazole, dibenzothiophene, dibenzofuran, dibenzodioxin and the like. Where Ar¹ and Ar² are each a fluorenyl group, the fluorenyl group may be 9,9-diphenylfluorene, 9,9-dimethylfluorene and the like. Where Ar¹ and Ar² are each aliphatic ring, the aliphatic ring may be preferably a C₃-C₃₀ aliphatic ring, more preferably, a C₃-C₁₂ aliphatic ring, for example, cyclohexane, cyclohexylcyclohexane, or the like. Where Ar¹ and Ar² are each an alkyl group, the alkyl group may be preferably a C₂-C₁₀ alkyl group, for example, methyl, t-butyl and the like. Where Ar¹ and Ar² are each an alkenyl group, the alkenyl group may be preferably a C₂-C₁₀ alkenyl group, for example, ethene, propene and the like.

L¹ to L³ are each independently selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

Where L¹ to L³ are each an arylene group, the arylene group may be preferably a C₆-C₃₀ arylene group, more preferably a C₆-C₁₈ arylene group, for example, phenyl, biphenyl, naphthyl, terphenyl and the like. Where L¹ to L³ are each a heterocyclic group, the heterocyclic group may be preferably a C₂-C₃₀ heterocyclic group, more preferably a C₂-C₁₈ heterocyclic group, for example, carbazole, phenylcarbazole, dibenzofuran, dibenzothiophene and the like.

R¹ is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)), and adjacent groups may be bonded to each other to form a ring.

a is an integer of 0-9, and where a is an integer of 2 or more, each of a plurality of R¹s are the same as or different from each other.

The ring formed by bonding between neighboring R¹s may be a C₆-C₆₀ aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring and the like. Where an aromatic ring is formed by bonding between neighboring R¹s, the aromatic ring may be preferably a C₆-C₃₀ aromatic ring group, more preferably, a C₆-C₁₄ aromatic ring group, for example, benzene, naphthalene, phenanthrene or the like.

Where R¹ is an aryl group, the aryl group may be preferably a C₆-C₃₀ aryl group, more preferably a C₆-C₁₈ aryl group, for example, phenyl, naphthyl, biphenyl, terphenyl, phenanthrene, and the like.

L′ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

R_(a) and R_(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

Preferably, compound derived from Formula 1-1 is excluded from Formula 1.

In Formula 1-1, each symbol is as defined for Formula 1. Preferably, Ar¹ and Ar² are each independently selected from the group consisting of a C₆-C₁₈ aryl group, a fluorenyl group, a C₂-C₁₆ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group.

Formula 1 may be represented by one of Formula 1-A, 1-A-1 to 1-A-6.

In Formulas 1-A, 1-A-1 to 1-A-6, Ar¹, Are, L′-L³, X₁, R¹ and a are the same as defined for Formula 1.

Preferably, when the compound represented by Formula 1-A is used as a single host material, a compound in which both the polycyclic ring including X₁ and the triazine moiety are adjacent to the same ring of L³ may be excluded. For example, the following compound may be excluded from Formula 1-A.

Preferably, Formula 1-A may be Formula 1-A-7.

In Formula 1-A-7, Ar¹, Ar², L², X₁, R¹ and a are the same as defined for Formula 1.

In addition, preferably, in Formula 1-A, L³ may be a C₁₀-C₂₀ arylene group; or a C₇-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P, more preferably, the arylene group and the heterocyclic group are a condensed ring condensed with two or more rings.

Also, preferably, in Formula 1-A, L¹-L³ may be a single bond or an aryl group (except for a phenyl group).

In addition, Formula 1 may be represented by Formula 1-B or 1-C.

In Formula 1-B or 1-C, each of symbols may be defined as follows.

Ar¹, Ar², L¹, L², X₁, R¹ and a are the same as defined for Formula 1.

X₃ is O or S.

R⁸ is independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a fused ring of a C₃-C₂₀ aliphatic ring with a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L^(a)-N(R^(a))(R^(b)), and adjacent groups may be linked to each other to form a ring.

i is an integer of 0-6, and where i is an integer of 2 or more, each of a plurality of R⁸s are the same as or different from each other.

L^(a) is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

R^(a) and R^(b) are each independently selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

In addition, Formula 1 may be represented by one of Formula 1-D, 1-D-1 and 1-D-2.

In Formula 1-D, 1-D-1 and 1-D-2, each of symbols may be defined as follows.

Ar¹, Ar², L¹, L², X₁, R¹ and a are the same as defined for Formula 1.

R⁹ is independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a fused ring of a C₃-C₂₀ aliphatic ring with a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L^(a)-N(R^(a))(R^(b)), and adjacent groups may be linked to each other to form a ring.

j is an integer of 0-6, and where j is an integer of 2 or more, each of a plurality of R⁹s are the same as or different from each other.

L^(a), R^(a) and R^(b) are the same as defined for Formula 1-B.

In addition, Formula 1 may be represented by Formula 1-E.

In Formula 1-E, Ar¹, L¹-L³, X₁, R¹ and a are the same as defined for Formula 1, and X₂ is O or S.

R⁴ is selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a ring of a C₃-C₂₀ aliphatic ring with a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L^(a)-N(R^(a))(R^(b)), and adjacent groups may be linked to each other to form a ring. Here, L^(a), R^(a) and R^(b) are the same as defined for Formula 1-B.

d is an integer of 0-7, and where d is an integer of 2 or more, each of a plurality of R⁴s are the same as or different from each other.

Preferably, Formula 1-E may be represented by one of Formulas 1-E-1 to 1-E-7.

In Formulas 1-E-1 to 1-E-7, each of symbols may be defined as follows.

Ar¹, L¹-L³, X₁, R¹ and a are the same as defined for Formula 1, and X₂ is O or S.

R₄ and R² may be defined the same as R⁴ defined in Formula 1-E. Thant is, R₄ and R² are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a ring of a C₃-C₂₀ aliphatic ring with a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L^(a)-N(R^(a))(R^(b)), and adjacent groups may be linked to each other to form a ring.

b and d are each an integer of 0-7, and where b is an integer of 2 or more, each of a plurality of R²s are the same as or different from each other, where d is an integer of 2 or more, each of a plurality of R₄s are the same as or different from each other.

In Formula 1-E, when both L² and L³ are a single bond and one of R⁴s is necessarily a specific substituent (that is, a substituent defined as Ar in Formula A) other than hydrogen, Formula 1-E may be represented by Formula A.

In Formulas A, each symbol may be defined as follows.

X₁, X₂, L¹, Ar¹ and a are the same as defined for Formula 1-E.

R¹ is hydrogen or deuterium.

R² and R³ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, and a C₆-C₂₀ aryloxy group, and adjacent groups may be linked to each other to form a ring.

b′ is an integer from 0 to 3, c is an integer from 0 to 4, and when each of these is an integer of 2 or more, multiple R²s are the same as or different from each other and multiple R³s are the same as or different from each other.

Ar is selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, and a C₆-C₂₀ aryloxy group, and adjacent groups may be linked to each other to form a ring.

The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and the ring formed by adjacent groups may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group.

Formula A may be represented by one of the following Formulas A-1 to A-4, and B-1 to B-4.

In Formulas A-1 to A-4 and B-1 to B-4, X₁, X₂, L¹, Ar¹, Ar, R¹ to R³, a, b′ and c are the same as defined for Formula A.

In Formula A, at least one of Ar¹ and Ar may be selected from the group consisting of Formulas Ar-1 to Ar-6.

In Formulas Ar-1 to Ar-6, each symbol may be defined as follows.

* indicates a binding site.

R₁₁ to R₁₆ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, and a C₆-C₂₀ aryloxy group, and adjacent groups may be linked to each other to form a ring.

q is an integer from 0 to 5, r and t are each an integer from 0 to 4, s is an integer from 0 to 3, and when each of these is an integer of 2 or more, multiple R₁₁s, multiple R₁₂s, multiple R₁₃s, multiple R₁₄s, multiple R₁₅s, multiple R₁₆s are the same as or different from each other.

Y is O, S, C(R^(x))(R^(y)) or N(R^(z)).

R^(x), R^(y), R^(z) and R_(b) are each independently selected from the group consisting of hydrogen, deuterium, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a C₁-C₂₀ alkyl group.

R^(a) is selected from the group consisting of a single bond, a C₁-C₂₀ alkylene group, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring, and R^(a) and R_(b) may be linked to each other to form a ring.

Preferably, in Formulas 1-A, 1-B and 1-C, Ar¹ and Ar² may be different from each other, Ar¹ or Ar² may be a naphthyl group.

In addition, preferably, in Formulas 1-B and 1-C, Ar¹ and Ar² may be each independently an aryl group.

Preferably, the ring formed by bonding between neighboring groups may be a C₆-C₆₀ aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring and the like. Where an aromatic ring is formed by bonding between neighboring groups, the aromatic ring may be preferably a C₆-C₃₀ aromatic ring group, more preferably, a C₆-C₁₄ aromatic ring group, for example, benzene, naphthalene, phenanthrene or the like.

Preferably, each symbol in the above Formulas may be further substituted. For example, in Formula 1, Formulas 1-A, 1-B, 1-C, 1-D and 1-E, Formulas 1-A-1 to 1-A-7, Formula 1-D-1, Formula 1-D-2, Formulas 1-E-1 to 1-E-7, Ar¹, Are, L¹, L^(a), R¹, R², R⁴, R₄, R⁸, R⁹, R_(a), R_(b), R^(a), R^(b), and the ring formed by bonding between adjacent groups may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group.

In another aspect of the present invention, the present invention provides an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises compound represented by Formula 1, preferably, one of Formula 1-A to Formula 1-C, more preferably, compound represented by one of Formula 1-A to Formula 1-C is comprised in a light emitting layer of the organic material layer.

In another aspect of the present invention, the present invention provides an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a phosphorescent light emitting layer, and the host of the phosphorescent light emitting layer comprises a first compound represented by Formula 1 and a second compound represented by Formula 2.

In Formula 2, each of symbols may be defined as follows.

Ar³ to Ar⁵ are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group, and Ar⁴ and Ar⁵ may be bonded to each other to form a ring. Here, the formed ring is a hetero ring containing one or more N.

n is an integer of 0-3, and where n is an integer of 2 or more, each of a plurality of Ar⁴s, and each of a plurality of Ar⁵s are the same as or different from each other.

Where Ar³ to Ar⁵ are each an aryl group, the aryl group may be preferably a C₆-C₃₀ aryl group, more preferably a C₆-C₁₈ aryl group, for example, phenyl, biphenyl, naphthyl, terphenyl, phenanthrene and the like. Where Ar³ to Ar⁵ are each a heterocyclic group, the heterocyclic group may be preferably a C₂-C₃₀ heterocyclic group, more preferably a C₂-C₁₈ heterocyclic group, for example, pyridine, pyrimidine, triazine, carbazole, phenylcarbazole, dibenzothiophene, dibenzofuran and the like. Where Ar³ to Ar⁵ are each a fluorenyl group, the fluorenyl group may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9′-spirobifluorene and the like.

L⁴ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

Where L⁴ is an arylene group, the arylene group may be preferably a C₆-C₃₀ arylene group, more preferably a C₆-C₁₈ arylene group, for example, phenyl, biphenyl, naphthyl, terphenyl and the like. Where L⁴ is a heterocyclic group, the heterocyclic group may be preferably a C₂-C₃₀ heterocyclic group, more preferably a C₂-C₁₈ heterocyclic group, more preferably a C₂-C₁₂ heterocyclic group, for example, pyridine, triazine, dibenzothiophene, dibenzofuran and the like. Where L⁴ is a fluorenyl group, the fluorenyl group may be 9,9-dimethylfluorene, 9,9-diphenylfluorene, 9,9′-spirobifluorene and the like.

R² and R³ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)), and adjacent groups may be bonded to each other to form a ring. Here, the ring formed by bonding between neighboring groups may be a C₆-C₆₀ aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring and the like.

Where an aromatic ring is formed by bonding between neighboring R²s or neighboring R³s, the aromatic ring may be preferably a C₆-C₃₀ aromatic ring group, more preferably, a C₆-C₁₄ aromatic ring group, for example, benzene, naphthalene, phenanthrene or the like.

Where an aromatic ring is formed by bonding between neighboring R²s or neighboring R³s, the aromatic ring may be preferably a C₆-C₃₀ aromatic ring group, more preferably, a C₆-C₁₄ aromatic ring group, for example, benzene, naphthalene, phenanthrene or the like.

b is an integer of 0-4, c is an integer of 0-3, and where each of these is an integer of 2 or more, each of a plurality of R²s, and each of a plurality of R³s are the same as or different from each other,

L′ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

R_(a) and R_(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

Formula 2 may be represented by Formula 2-A or Formula 2-B.

In Formulas 2-A and 2-B, wherein, L⁴, Ar³ to Ar⁵, R², R³, b and c are the same as defined for Formula 2.

In addition, Formula 2 may be represented by one of Formula 2-C to Formula 2-F.

In Formulas 2-C to Formula 2-F, each symbol can be defined as follows.

Ar³ to Ar⁵, R², R³, b and c are the same as defined for Formula 2.

R¹⁰ to R¹³ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₂₀ aryloxy group, -L^(a)-N(R^(a))(R^(b)) and a combination thereof, and adjacent groups may be linked to each other to form a ring.

The ring formed by bonding between neighboring groups may be a C₆-C₆₀ aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring and the like.

Where an aromatic ring is formed by bonding between neighboring R¹⁰s, R¹¹s, R¹²s or neighboring R¹³s, the aromatic ring may be preferably a C₆-C₃₀ aromatic ring group, more preferably, a C₆-C₁₄ aromatic ring group, for example, benzene, naphthalene, phenanthrene or the like.

k and l are each an integer of 0-4, n and m are each an integer of 0-3, and where each of these is an integer of 2 or more, each of a plurality of R¹⁰, each of a plurality of R¹¹, each of a plurality of R¹², and each of a plurality of R¹³ are the same as or different from each other.

V is N-(L^(a)-Ar^(a)), O, S or C(R′)(R″).

R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a fused ring of a C₃-C₂₀ aliphatic ring with a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₂₀ aryloxy group and -L^(a)-N(R^(a))(R^(b)), and R′ and R″ may be linked to each other to form a ring.

Ar^(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

L^(a) is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

R^(a) and R_(b) are each independently selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

Formula 2 may be represented by one of the following Formula 2-G to Formula 2-T.

In Formulas 2-G to 2-T, Ar³ to Ar⁵, L⁴, R², R³, b and c are the same as defined for Formula 2.

Formula 2 may be represented by Formula 2-U.

In Formula 2-U, each of symbols may be defined as follows.

Ar³, Ar⁵, L⁴, R², R³, b, c and n are the same as defined for Formula 2.

U is N-(L^(a)-Ar^(a)), O, S or C(R′)(R″).

R¹⁴ and R¹⁵ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a fused ring of a C₃-C₂₀ aliphatic ring with a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₂₀ aryloxy group and -L^(a)-N(R^(a))(R^(b)), and adjacent groups may be linked to each other to form a ring. The ring formed by bonding between neighboring groups may be a C₆-C₆₀ aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring and the like.

Where an aromatic ring is formed by bonding between neighboring R¹⁴s or neighboring R¹⁵s, the aromatic ring may be preferably a C₆-C₃₀ aromatic ring group, more preferably, a C₆-C₁₄ aromatic ring group, for example, benzene, naphthalene, phenanthrene or the like.

o is an integer of 0-3, p is an integer of 0-4, and where each of these is an integer of 2 or more, each of a plurality of R¹⁴, and each of a plurality of R¹⁵ are the same as or different from each other.

R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a fused ring of a C₃-C₂₀ aliphatic ring with a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₃₀ aryloxy group, and -L^(a)-N(R^(a))(R^(b)), and R′ and R″ may be linked to each other to form a ring.

Ar^(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

L^(a) is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

R^(a) and R^(b) are each independently selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

Each symbol in Formula 2 and Formulas 2-A to 2-U may be further substituted. For example, Ar³-Ar⁵, R², R³, R¹⁰ to R¹⁵, L⁴, L¹, L^(a), Ar^(a), R_(a), R_(b), R′, R″, R^(a), R^(b) and the ring formed by bonding between adjacent groups may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group.

Preferably, in Formulas 1 and 2, L¹ to L⁴ may be each independently one of the following Formulas b-1 to b-13.

In Formulas b-1 to b-13, each of symbols may be defined as follows.

R⁵ to R⁷ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a fused ring of a C₃-C₂₀ aliphatic ring with a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L^(a)-N(R^(a))(R^(b)), and adjacent groups may be bonded to each other to form a ring. The ring formed by bonding between neighboring groups may be a C₆-C₆₀ aromatic ring group, a fluorenyl group, a C₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring or a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring and the like.

Where an aromatic ring is formed by bonding between neighboring R⁵s, neighboring R⁶s or neighboring R⁷s, the aromatic ring may be preferably a C₆-C₃₀ aromatic ring group, more preferably, a C₆-C₁₄ aromatic ring group, for example, benzene, naphthalene, phenanthrene or the like.

Y is N-(L^(a)-Ar^(a)), O, S or C(R′)(R″).

Z¹ to Z³ are each independently C, C(R′) or N, and at least one of Z¹ to Z³ is N.

f is an integer of 0-6, e, g, h and i are each an integer of 0-4, j and k are each an integer of 0-3, l is an integer of 0-2, m is an integer of 0-3, and where each of these is an integer of 2 or more, each of a plurality of R⁵, each of a plurality of R⁶, and each of a plurality of R⁷ are the same as or different from each other.

R′ and R″ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a fused ring of a C₃-C₂₀ aliphatic ring with a C₆-C₂₀ aromatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, a C₆-C₃₀ aryloxy group, and -L^(a)-N(R^(a))(R^(b)).

R′ and R″ in C(R′)(R″) may be linked to each other to form a ring, and adjacent R¹s in C(R′) may be linked to each other to form a ring.

Ar^(a) is selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

L^(a) is selected from the group consisting of a single bond, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

R^(a) and R^(b) are each independently selected from the group consisting of a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a combination thereof.

R⁵ to R⁷, L^(a), Ar^(a), R′, R″, R^(a), R^(b) and the ring formed by bonding between adjacent groups may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group.

Specifically, the compound represented by formula 1 may be one of the following compounds, but there is no limitation thereto.

Specifically, the compound represented by formula A may be one of the following compounds, but there is no limitation thereto.

Specifically, the compound represented by formula 2 may be one of the following compounds, but there is no limitation thereto.

In another aspect, the present invention provides an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, wherein the organic material layer comprises a light emitting layer formed between the first electrode and the second electrode.

In another aspect, the present invention provides an electronic device including a display device comprising the organic electric element and a controller for driving the display device.

In an embodiment, the light emitting layer includes the compound represented by Formula A.

In addition, the light emitting layer may include at least one of compound represented by the following Formula G or compound represented by the following Formula H, and compound represented by Formula A.

In the above Formulas, each symbol may be defined as follows.

Z¹ to Z¹⁶ are each independently C(R) or N, W is N(Ar¹³), O, S or C(R′)(R″), and v is C(R^(a)). With the proviso that in Formula H, Formula H-1 is bonded to at least one pair of adjacent v, and the remaining vs are C(R^(a)). In Formula H-1, * represents a binding site.

Ar¹⁰ to Ar¹³ are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, and -L′-N(R_(a))(R_(b)).

L¹⁰ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

R²¹, R²², R, R′, R″, R^(a) are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₂₀ aryloxy group and -L′-N(R_(a))(R_(b)), and adjacent groups may be bonded to each other to form a ring, and R′ and R″ may be bonded to each other to form a ring.

L′ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

R_(a) and R_(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring.

The aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, the ring formed by adjacent groups and the ring formed by R′ and R″ may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group.

Formula G may be represented by one of the following Formulas G-1 to G-4.

In Formulas G-1 to G-4, each symbol is the same as defined for Formula G. That is, Z¹ to Z¹⁶, Ar¹⁰, Ar¹³, L¹⁰, R′ and R″ are the same as defined for Formula G.

Formula H may be represented by the following Formula H-2.

In Formula H-2, each symbol is the same as defined for Formula H. That is, Ar¹¹, Ar¹², R²¹, R²², r and s are the same as defined for Formula H, R²³ is the same as R^(a) as defined in Formula H, and t is an integer of 0 to 2.

Specifically, the compound represented by formula G may be one of the following compounds, but there is no limitation thereto.

Specifically, the compound represented by formula H may be one of the following compounds, but is not limited thereto.

Hereinafter, examples for synthesizing the compounds represented by Formulas 1 and 2, Formula A, Formula G, Formula H according to the present invention and examples for preparing an organic electric element according to the present invention will be described in detail with reference to examples, but the present invention is not limited to the following examples.

[Synthesis Example 1] Formula 1

The compound represented by Formula 1 according to the present invention can be synthesized by reacting Sub 1 and Sub 2 as shown in Reaction Scheme 1, but there is no limitation thereto.

Compounds belong to Sub 1 of Reaction Scheme 1 are as follows, but are not limited thereto.

FD-MS values of compounds belong to Sub 1 are shown in Table 1 below.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-1 m/z = 267.06(C₁₅H₁₀ClN₃ = 267.72) Sub 1-2 m/z = 317.07(C₁₉H₁₂ClN₃ = 317.78) Sub 1-3 m/z = 507.15(C₃₄H₂₂ClN₃ = 508.02) Sub 1-4 m/z = 317.07(C₁₉H₁₂ClN₃ = 317.78) Sub 1-5 m/z = 272.09(C₁₅H₅D₅ClN₃ = 272.75) Sub 1-6 m/z = 367.09(C₂₃H₁₄ClN3 = 367.84) Sub 1-7 m/z = 507.15(C₃₄H₂₂ClN₃ = 508.02) Sub 1-8 m/z = 419.12(C₂₇H₁₈ClN₃ = 419.91) Sub 1-9 m/z = 343.09(C₂₁H₁₄ClN₃ = 343.81) Sub 1-10 m/z = 367.09(C₂₃H₁₄ClN₃ = 367.84) Sub 1-11 m/z = 433.13(C₂₈H₂₀ClN₃ = 433.94) Sub 1-12 m/z = 419.12(C₂₇H₁₈ClN₃ = 419.91) Sub 1-13 m/z = 394.1(C₂₄H₁₅ClN₄ = 394.86) Sub 1-14 m/z = 443.12(C₂₉H₁₈ClN₃ = 443.93) Sub 1-15 m/z = 494.13(C₃₂H₁₉ClN₄ = 494.98) Sub 1-16 m/z = 393.1(C₂₅H₁₆ClN₃ = 393.87) Sub 1-17 m/z = 469.13(C₃₁H₂₀ClN₃ = 469.97) Sub 1-18 m/z = 469.13(C₃₁H₂₀ClN₃ = 469.97) Sub 1-19 m/z = 393.1(C₂₅H₁₈ClN₃ = 393.87) Sub 1-20 m/z = 508.15(C₃₃H₂₁ClN₄ = 509.01) Sub 1-21 m/z = 551.12(C₃₅H₂₂ClN₃S = 552.09) Sub 1-22 m/z = 4223.06(C₂₅H₁₄ClN₃S = 509.01) Sub 1-23 m/z = 393.1(C₂₅H₁₆ClN₃ = 393.87) Sub 1-24 m/z = 292.05(C₁₆H₉ClN₄ = 292.73) Sub 1-25 m/z = 405.1(C₂₅H₁₆ClN₃ = 405.89) Sub 1-26 m/z = 419.12(C₂₇H₁₈ClN₄ = 419.91) Sub 1-27 m/z = 393.1(C₂₅H₁₈ClN₃ = 393.87) Sub 1-28 m/z = 394.1(C₂₄H₁₅ClN₄ = 394.86) Sub 1-29 m/z = 523.11(C₃₃H₁₈ClN₃O₂ = 523.98) Sub 1-30 m/z = 525.11(C₃₃H₂₀ClN₃S = 526.05) Sub 1-31 m/z = 373.04(C₂₁H₁₂ClN₃S = 373.86) Sub 1-32 m/z = 373.04(C₂₁H₁₂ClN₃S = 373.86) Sub 1-33 m/z = 433.1(C₇₇H₁₈ClN₃O = 433.9) Sub 1-34 m/z = 500.09(C₃₀H₁₇ClN₄S = 501) Sub 1-35 m/z = 499.09(C₃₁H₁₈ClN₃S = 500.02) Sub 1-36 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.9) Sub 1-37 m/z = 357.07(C₂₁H₁₂ClN₃O = 357.8) Sub 1-38 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.9) Sub 1-39 m/z = 525.11(C₃₃H₂₀ClN₃S = 526.05) Sub 1-40 m/z = 499.09(C₃₁H₁₈ClN₃S = 500.02) Sub 1-41 m/z = 433.1(C_(Z7)H₁₆ClN₃O = 433.9) Sub 1-42 m/z = 473.13(C₃₀H₂₀ClN₃O = 473.96) Sub 1-43 m/z = 473.08(C₂₉H₁₆ClN₃S = 473.98) Sub 1-44 m/z = 482.13(C₃₁H₁₉ClN₄ = 482.97)

Compounds belong to Sub 2 of Reaction Scheme 1 are as follows, but are not limited thereto.

FD-MS values of compounds belong to Sub 2 are shown in Table 2 below.

TABLE 2 Compound FD-MS Compound FD-MS Sub 2-1 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 2-2 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 2-3 m/z = 420.19(C₂₈H₂₅BO₃ = 420.32) Sub 2-4 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 2-5 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 2-6 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 2-7 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 2-8 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 2-9 m/z = 510.2(C₃₄H₂₇BO₄ = 510.4) Sub 2-10 m/z = 510.2(C₃₄H₂₇BO₄ = 510.4) Sub 2-11 m/z = 420.19(C₂₈H₂₅BO₃ = 420.32) Sub 2-12 m/z = 420.19(C₂₈H₂₅BO₃ = 420.32) Sub 2-13 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 2-14 m/z = 526.18(C₃₄H₂₇BO₃S = 526.46) Sub 2-15 m/z = 526.18(C₃₄H₂₇BO₃S = 526.46) Sub 2-16 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 2-17 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 2-18 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 2-19 m/z = 420.19(C₂₈H₂₅BO₃ = 420.32) Sub 2-20 m/z = 420.19(C_(2B)H₂₅BO₃ = 420.32) Sub 2-21 m/z = 420.19(C₂₈H₂₅BO₃ = 420.32) Sub 2-22 m/z = 420.19(C₂₈H₂₅BO₃ = 420.32) Sub 2-23 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 2-24 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 2-25 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 2-26 m/z = 510.2(C₃₄H₂₇BO₄ = 510.4) Sub 2-27 m/z = 510.2(C₃₄H₂₇BO₄ = 510.4) Sub 2-28 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 2-29 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 2-30 m/z = 420.19(C₂₈H₂₅BO₃ = 420.32) Sub 2-31 m/z = 420.19(C₂₈H₂₅BO₃ = 420.32) Sub 2-32 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 2-33 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 2-34 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 2-35 m/z = 526.18(C₃₄H₂₇BO₃S = 526.46) Sub 2-36 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 2-37 m/z = 526.18(C₃₄H₂₇BO₃S = 526.46) Sub 2-38 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 2-39 m/z = 510.2(C₃₄H₂₇BO₄ = 510.4) Sub 2-40 m/z = 510.2(C₃₄H₂₇BO₄ = 510.4) Sub 2-41 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 2-42 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub 2-43 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 2-44 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 2-45 m/z = 526.18(C₃₄H₂₇BO₃S = 526.46) Sub 2-46 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 2-47 m/z = 470.21(C₃₂H₂₇BO₃ = 470.38) Sub 2-48 m/z = 526.18(C₃₄H₂₇BO₃S = 526.46) Sub 2-49 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub 2-50 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28)

1. Synthesis Example of Sub 1

Sub 1 of Reaction Scheme 1 may be synthesized by the reaction route of the following Reaction Scheme 2, but are not limited thereto.

Synthesis Example of Sub 1-7

2,4-dichloro-6-phenyl-1,3,5-triazine (30 g, 132.71 mmol) was dissolved in THF 600 mL, and 2-(9,9-diphenyl-9H-fluoren-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (70.77 g, 159.25 mmol), Pd(PPh₃)₄ (7.67 g, 6.64 mmol), K₂CO₃ (55.02 g, 398.12 mmol) and water (300 ml) were added to the solution. Then, the mixture was stirred under reflux. When the reaction was completed, the reaction product was extracted by ether and water. The organic layer was concentrated and the concentrate was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 51.24 g (yield: 76%) of the product.

Synthesis Example of Sub 1-29

2,4-dichloro-6-(dibenzo[b,d]furan-4-yl)-1,3,5-triazine (20 g, 63.26 mmol) was dissolved in THF 450 mL, and 2-(4-(dibenzo[b,d]furan-1-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (28.11 g, 75.92 mmol), Pd(PPh₃)₄ (3.66 g, 3.16 mmol), K₂CO₃ (26.23 g, 189.79 mmol) and water 150 mL were added to the solution. Then, the reaction was carried out in the same manner as in the synthesis method of Sub 1-7 to obtain 69.7 g (yield: 73%) of the product.

Synthesis Example of Sub 1-39

2-([1,1′:3′,1″-terphenyl]-5′-yl)-4,6-dichloro-1,3,5-triazine (17 g, 44.94 mmol) was dissolved in THF 340 mL, and 2-(dibenzo[b,d]thiophen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (16.73 g, 53.93 mmol), Pd(PPh₃)₄ (2.6 g, 2.25 mmol), K₂CO₃ (18.63 g, 134.83 mmol) and water 170 mL were added to the solution. Then, the reaction was carried out in the same manner as in the synthesis method of Sub 1-7 to obtain 69.7 g (yield: 73%) of the product.

2. Synthesis Example of Sub 2

Sub 2 of Reaction Scheme 1 may be synthesized by the reaction route of the following Reaction Scheme 3, but are not limited thereto.

Synthesis Example of Sub 2-4

Bis(pinacolato)diboron (CAS Registry Number: 73183-34-3) (11.7 g, 46.07 mmol), PdCl₂(dppf) (1.3 g, 1.77 mmol), KOAc (10.4 g, 106.31 mmol) and DMF (300 ml) were added to 6-(4-bromonaphthalen-2-yl)naphtho[1,2-b]benzofuran (15 g, 35.44 mmol). Then, the mixture was stirred under reflux. When the reaction was completed, an organic layer of the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 12.83 g (yield: 77%) of the product.

Synthesis Example of Sub 2-25

Bis(pinacolato)diboron (CAS registry number, 73183-34-3) (26.35 g, 103.76 mmol), PdCl₂(dppf) (3.08 g, 4.21 mmol), KOAc (24.77 g, 252.4 mmol) and DMF (500 ml) were added to 8-bromobenzo[b]naphtho[2,1-d]thiophene (25 g, 79.82 mmol). Then, the mixture was stirred under reflux. When the reaction was completed, an organic layer of the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 24 g (yield: 83%) of the product.

3. Synthesis Example of Final Products Synthesis Example of 1-13

Sub 1-11 (34.7 g, 80 mmol), Sub 2-25 (30.9 g, 80 mmol), K₂CO₃ (19.3 g, 140 mmol) and Pd(PPh₃)₄ (2.8 g, 2.4 mmol) were dissolve in THF and water in a round bottom flask, and the mixture was refluxed at 80° C. for 12 hours. When the reaction was completed, the reaction product was cooled to room temperature, extracted with CH₂Cl₂ and washed with water. An organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column to obtain 37.4 g (yield: 71%) of the product.

Synthesis Example of 1-27

The reaction was carried out in the same manner as in the synthesis method of 1-13, using Sub 1-13 (44.6 g, 80 mmol) instead of Sub 1-11 and Sub 2-43 (30.9 g, 80 mmol) instead of Sub 2-25 to obtain 43.2 g (yield: 69%) of the product.

Synthesis Example of 1-34

The reaction was carried out in the same manner as in the synthesis method of 1-13, using Sub 1-34 (42.7 g, 80 mmol) instead of Sub 1-11 and Sub 2-18 (34.9 g, 80 mmol) instead of Sub 2-25 to obtain 42.7 g (yield: 66%) of the product.

Synthesis Example of 1-45

The reaction was carried out in the same manner as in the synthesis method of 1-13, using Sub 1-37 (40.8 g, 80 mmol) instead of Sub 1-11 and Sub 2-49 (43.1 g, 80 mmol) instead of Sub 2-25 to obtain 51.0 g (yield: 72%) of the product.

Synthesis Example of 1-53

The reaction was carried out in the same manner as in the synthesis method of 1-13, using Sub 1-1 (40.8 g, 80 mmol) instead of Sub 1-11 and Sub 2-51 (37.0 g, 80 mmol) instead of Sub 2-25 to obtain 45.4 g (yield: 70%) of the product.

Synthesis Example of 1-88

The reaction was carried out in the same manner as in the synthesis method of 1-13, using Sub 1-4 (44.0 g, 80 mmol) instead of Sub 1-11 and Sub 2-16 (29.6 g, 80 mmol) instead of Sub 2-25 to obtain 41.2 g (yield: 68%) of the product.

The FD-MS values of compounds 1-1 to 1-124 of the present invention synthesized by the same method as in Synthesis Example are shown in Table 3 below.

TABLE 3 Compound FD-MS Compound FD-MS 1-1 m/z = 465.1 3(C₃₁H₁₉N₃S-465.57) 1-2 m/z = 575.2(C₄₁H₂₅N₃O = 575.67) 1-3 m/z = 705.22(C₅₀H₃₁N₃S = 705.88) 1-4 m/z = 540.14(C₃₆H₂₀N₄S = 540.64) 1-5 m/z = 546.19(C₃₇H₁₈D₅N₃S = 546.7) 1-6 m/z = 549.18(C₃₉H₂₃N₃O = 549.63) 1-7 m/2 = 591.18(C₄₁H₂₅N₃S = 591.73) 1-8 m/z = 465.13(C₃₁H₁₉N₃S = 465.57) 1-9 m/z = 705.22(C₅₀H₃₁N₃S = 705.88) 1-10 m/z = 617.19(C₄₃H₂₇N₃S = 617.77) 1-11 m/z = 601.22(C₄₃H₂₇N₃O = 601.71) 1-12 m/z = 565.16(C₃₉H₂₃N₃S = 565.69) 1-13 m/z = 631.21(C₄₄H₂₉N₃S = 631.8) 1-14 m/z = 499.17(C₃₅H₂₁N₃O = 499.57) 1-15 m/z = 617.19(C₄₃H₂₇N₃S = 617.77) 1-16 m/z = 603.18(C₄₂H₂₅N₃S = 603.74) 1-17 m/z = 753.28(C₅₅H₃₅N₃O = 753.91) 1-18 m/z = 592.17(C₄₀H₂₄N₄S = 592.72) 1-19 m/z = 641.19(C₄₅H₂₇N₃S = 641.79) 1-20 m/z = 692.2(C₄₈H₂₈N₄S = 692.84) 1-21 m/z = 575.2(C₄₁H₂₅N₃O = 575.67) 1-22 m/z = 591.18(C₄₁H₂₅N₃S = 591.73) 1-23 m/z = 667.21(C₄₇H₂₉N₃S = 667.83) 1-24 m/z = 575.2(C₄₁H₂₅N₃O = 575.67) 1-25 m/z = 591.18(C₄₁H₂₅N₃S = 591.73) 1-26 m/z = 575.2(C₄₁H₂₅N₃O = 575.67) 1-27 m/z = 592.17(C_(4O)H₂₄N₄S = 592.72) 1-28 m/z = 575.2(C₄₁H₂₅N₃O = 575.67) 1-29 m/z = 706.22(C₄₉H₃₀N₄S = 706.87) 1-30 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 1-31 m/z = 621.13(C₄₁H₂₃N₃S₂ = 621.78) 1-32 m/z = 555.14(C₃₇H₂₁N₃OS = 555.66) 1-33 m/z = 615.19(C₄₃H₂₅N₃O₂ = 615.69) 1-34 m/z = 698.16(C₄₅H₂₆N₄S₂ = 698.86) 1-35 m/z = 697.16(C₄₇H₂₇N₃S₂ = 697.87) 1-36 m/z = 615.19(C₄₃H₂₅N₃O₂ = 615.69) 1-37 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-38 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) 1-39 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-40 m/z = 655.23(C₄₆H₂₉N₃O₂ = 655.76) 1-41 m/z = 671.15(C₄₅H₂₅N₃S₂ = 671.84) 1-42 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-43 m/z = 571.12(C₃₇H₂₁N₃S₂ = 571.72) 1-44 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-45 m/z = 555.14(C₃₇H₂₁N₃OS = 555.66) 1-46 m/z = 721.18(C₄₉H₂₇N₃O₂S = 721.83) 1-47 m/2 = 690.24(C₄₉H₃₀N₄O = 690.81) 1-48 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) 1-49 m/z = 647.15(C₄₃H₂₅N₃S₂ = 647.81) 1-50 m/z = 697.16(C₄₇H₂₇N₃S₂ = 697.87) 1-51 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-52 m/z = 756.23(C₅₃H₃₂N₄S = 756.93) 1-53 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-54 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-55 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-56 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) 1-57 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) 1-58 m/z = 874.28(C₆₁H₃₈N₄OS = 875.06) 1-59 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-60 m/z = 905.3(C₆₆H₃₉N₃O₂ = 906.06) 1-61 m/z = 615.19(C₄₃H₂₅N₃O₂ = 615.69) 1-62 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1-63 m/z = 713.25(C₄₉H₃₅N₃OS = 713.9) 1-64 m/z = 721.18(C₄₉H₂₇N₃O₂S = 721.83) 1-65 m/z = 753.14(C₄₉H₂₇N₃S₃ = 753.96) 1-66 m/z = 737.18(C₄₉H₂₇N₃O₃S = 737.83) 1-67 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) 1-68 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-69 m/z = 657.19(C₄₅H₂₇N₃OS = 657.79) 1-70 m/z = 615.19(C₄₃H₂₅N₃O₂ = 615.69) 1-71 m/z = 773.2(C₅₃H₃₁N₃S₂ = 773.97) 1-72 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-73 m/z = 796.23(C₅₅H₃₂N₄OS = 796.95) 1-74 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-75 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) 1-76 m/z = 787.18(C₅₃H₂₉N₃OS₂ = 787.96) 1-77 m/z = 641.19(C₄₅H₂₇N₃S = 641.79) 1-78 m/z = 752.26(C₅₄H₃₂N₄O = 752.88) 1-79 m/z = 641.19(C₄₅H₂₇N₃S = 641.79) 1-80 m/z = 717.22(C₅₁H₃₁N₃S = 717.89) 1-81 m/z = 718.22(C₅₀H₁₃₀N₄S = 718.88) 1-82 m/z = 625.22(C₄₅H₂₇N₃O = 625.73) 1-83 m/z = 641.19(C₄₅H₂₇N₃S = 641.79) 1-84 m/z = 625.22(C₄₅H₂₇N₃O = 625.73) 1-85 m/z = 675.23(C₄₉H₂₉N₃O = 675.79) 1-86 m/z = 641.19(C₄₅H₂₇N₃S = 641.79) 1-87 m/z = 641.19(C₄₅H₂₇N₃S = 641.79) 1-88 m/z = 625.22(C₄₅H₂₇N₃O = 625.73) 1-89 m/z = 717.22(C₅₁H₃₁N₃S = 717.89) 1-90 m/z = 717.22(C₅₁H₃₁N₃S = 717.89) 1-91 m/z = 817.31(C₆₀H₃₉N₃O = 817.99) 1-92 m/z = 717.22(C₅₁H₃₁N₃S = 717.89) 1-93 m/z = 823.21(C₅₇H₃₃N₃S₂ = 824.03) 1-94 m/z = 715.23(C₅₁H₂₉N₃O₂ = 715.81) 1-95 m/z = 731.2(C₅₁H₂₉N₃OS = 731.87) 1-96 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97) 1-97 m/z = 791.26(C₅₇H₃₃N₃O₂ = 791.91) 1-98 m/z = 823.21(C₅₇H₃₃N₃S₂ = 824.03) 1-99 m/z = 913.22(C₆₃H₃₅N₃OS₂ = 914.11) 1-100 m/z = 823.21(C₅₇H₃₃N₃S₂ = 824.03) 1-101 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-102 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) 1-103 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1-104 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-105 m/z = 731.2(C₅₁H₂₉N₃OS = 731.87) 1-106 m/z = 831.23(C₅₉H₃₃N₃OS = 831.99) 1-107 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-108 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1-109 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) 1-110 m/z = 681.19(C₄₇H₂₇N₃OS = 681.81) 1-111 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 1-112 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97) 1-113 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1-114 m/z = 707.2(C₄₉H₂₉N₃OS = 707.85) 1-115 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 1-116 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 1-117 m/z = 841.27(C₆₁H₃₅N₃O₂ = 841.97) 1-118 m/z = 807.23(C₅₇H₃₃N₃OS = 807.97) 1-119 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) 1-120 m/z = 843.29(C₆₁H₃₇N₃O₂ = 843.99) 1-121 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) 1-122 m/z = 907.27(C₆₅H₃₇N₃OS = 908.09) 1-123 m/z = 867.29(C₆₃H₃₇N₃O₂ = 868.01) 1-124 m/z = 775.21(C₅₃H₃₀FN₃OS = 775.9)

[Synthesis Example 2] Synthesis Example Formula 2

The compound (Final product 2) represented by Formula 2 of the present invention may be prepared by reacting Sub 3 and Sub 4 as shown in Reaction Scheme 4 below, but is not limited thereto.

The compounds belonging to Sub 3 of Reaction Scheme 4 are as follows, but are not limited thereto.

The FD-MS values of the compounds belonging to Sub 3 are shown in Table 4 below.

TABLE 4 Compound FD-MS Compound FD-MS Sub 3-1 m/z = 321.02(C₁₈H₁₂BrN = 322.21) Sub 3-2 m/z = 321.02(C₁₈H₁₂BrN = 322.21) Sub 3-3 m/z = 397.05(C₂₄H₁₆BrN = 398.30) Sub 3-4 m/z = 563.12(C₃₇H₂₆BrN = 564.53) Sub 3-5 m/z = 397.05(C₂₄H₁₈BrN = 398.30) Sub 3-6 m/z = 397.05(C₂₄H₁₆BrN = 398.30) Sub 3-7 m/z = 473.08(C₃₀H₂₀BrN = 474.40) Sub 3-8 m/z = 473.08(C₃₀H₂₀BrN = 474.40) Sub 3-9 m/z = 473.08(C₃₀H₂₀BrN = 474.40) Sub 3-10 m/z = 473.08(C₃₀H₂₀BrN = 474.40) Sub 3-11 m/z = 473.08(C₃₀H₂₀BrN = 474.40) Sub 3-12 m/z = 473.08(C₃₀H₂₀BrN = 474.40) Sub 3-13 m/z = 497.08(C₃₂H₂₀BrN = 498.42) Sub 3-14 m/z = 503.03(C₃₀H₁₈BrNS = 504.45) Sub 3-15 m/z = 487.06(C₃₀H₁₈BrNO = 488.38) Sub 3-16 m/z = 513.11(C₃₃H₂₄BrN = 514.47) Sub 3-17 m/z = 473.08(C₃₀H₂₀BrN = 474.40) Sub 3-18 m/z = 628.13(C₃₉H₂₅BrN₄ = 629.56) Sub 3-19 m/z = 589.14(C₃₉H₂₈BrN = 590.56) Sub 3-20 m/z = 627.13(C₄₀H₂₆BrN₃ = 628.57) Sub 3-21 m/z = 473.08(C₃₀H₂₀BrN = 474.40) Sub 3-22 m/z = 474.96(C₂₄H₁₅Br₂N = 477.20) Sub 3-23 m/z = 550.99(C₃₀H₁₉Br₂N = 553.30) Sub 3-24 m/z = 580.94(C₃₀H₁₇Br₂N = 580.34) Sub 3-25 m/z = 477.94(C₂₁H₁₂Br₂N₄ = 480.16) Sub 3-26 m/z = 630.01(C₃₃H₂₀Br₂N₄ = 632.36) Sub 3-27 m/z = 574.99(C₃₂H₁₉Br₂N = 577.32) Sub 3-28 m/z = 550.99(C₃₀H₁₉Br₂N = 553.30) Sub 3-29 m/z = 524.97(C₂₈H₁₇Br₂N = 527.26) Sub 3-30 m/z = 524.97(C₂₈H₁₇Br₂N = 527.26) Sub 3-31 m/z = 574.99(C₃₂H₁₉Br₂N = 577.32) Sub 3-32 m/z = 513.11(C₃₃H₂₄BrN = 514.47)

The compounds belonging to Sub 4 of Reaction Scheme 4 are as follows, but are not limited thereto.

The FD-MS values of the compounds belonging to Sub 4 are shown in Table 5 below.

TABLE 5 Compound FD-MS Compound FD-MS Sub 4-1 m/z = 169.09(C₁₂H₁₁N = 169.22) Sub 4-2 m/z = 245.12(C₁₈H₁₅N = 245.32) Sub 4-3 m/z = 245.12(C₁₈H₁₅N = 245.32) Sub 4-4 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 4-5 m/z = 321.15 (C₂₄H₁₉N = 321.41) Sub 4-6 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 4-7 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 4-8 m/z = 295.14(C₂₂H₁₇N = 295.38) Sub 4-9 m/z = 409.18(C₃₁H₂₃N = 409.52) Sub 4-10 m/z = 483.20(C₃₇H₂₅N = 483.60) Sub 4-11 m/z = 459.20(C₃₅H₂₅N = 459.58) Sub 4-12 m/z = 485.21(C₃₇H₂₇N = 485.62) Sub 4-13 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 4-14 m/z = 335.13(C₂₄H₁₇NO = 335.40) Sub 4-15 m/z = 297.13(C₂₀H₁₅N₃ = 297.35) Sub 4-16 m/z = 219.10(C₁₆H₁₃N = 219.28) Sub 4-17 m/z = 249.12(C₁₇H₁₅NO = 249.31) Sub 4-18 m/z = 197.12(C₁₄H₁₅N = 197.28) Sub 4-19 m/z = 229.11(C₁₄H₁₅NO₂ = 229.27) Sub 4-20 m/z = 174.12(C₁₂H₆D₅N = 174.25) Sub 4-21 m/z = 281.21(C₂₀H₂₇N = 281.44) Sub 4-22 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 4-23 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 4-24 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 4-25 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 4-26 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 4-27 m/z = 297.13(C₂₀H₁₅N₃ = 297.35) Sub 4-28 m/z = 499.20(C₃₆H₂₅N₃ = 499.60) Sub 4-29 m/z = 499.20(C₃₆H₂₂N₂ = 410.51) Sub 4-30 m/z = 424.16(C₃₀H₂₀N₂O = 424.49) Sub 4-31 m/z = 440.13(C₃₀H₂₀N₂S = 440.56) Sub 4-32 m/z = 384.16(C₂₈H₂₀N₂ = 384.47) Sub 4-33 m/z = 334.15(C₂₄H₁₈N₂ = 334.41) Sub 4-34 m/z = 450.21(C₃₃H₂₆N₂ = 450.57) Sub 4-35 m/z = 410.18(C₃₀H₂₂N₂ = 410.51) Sub 4-36 m/z = 410.18(C₃₀H₂₂N₂ = 410.51) Sub 4-37 m/z = 575.24(C₄₂H₂₉N₃ = 575.70) Sub 4-38 m/z = 574.24(C₄₃H₃₀N₂ = 574.71) Sub 4-39 m/z = 460.19(C₃₄H₂₄N₂ = 460.57) Sub 4-40 m/z = 460.19(C₃₄H₂₄N₂ = 460.57) Sub 4-41 m/z = 461.19(C₃₃H₂₃N₃ = 461.56) Sub 4-42 m/z = 626.27(C₄₇H₃₄N₂ = 626.79) Sub 4-43 m/z = 565.23(C₃₉H₂₇N₅ = 565.67) Sub 4-44 m/z = 415.21(C₃₀H₁₇D₅N₂ = 415.54) Sub 4-45 m/z = 486.21(C₃₆H₂₆N₃ = 486.61) Sub 4-46 m/z = 415.21(C₃₀H₁₇D₅N₂ = 415.54)

1. Synthesis Example of Sub 3

Sub 3 may be synthesized by the reaction route of the following Reaction Scheme 4-1, but are not limited thereto.

Synthesis Example of Sub 3-c(1)

3-bromo-9-phenyl-9H-carbazole (45.1 g, 140 mmol) was dissolved in DMF (980 mL), and bispinacolborate (39.1 g, 154 mmol), PdCl₂(dppf) (3.43 g, 4.2 mmol) and KOAc (41.3 g, 420 mmol) were sequentially added to the solution. Then, the mixture was stirred for 24 hours and the obtained intermediate was separated by a silica gel column and recrystallized to obtain 35.2 g (yield: 68%) of a final compound.

Synthesis Example of Sub 3-c(2)

2-bromo-9-phenyl-9H-carbazole (76.78 g, 238.3 mmol) was dissolved in DMF (980 mL), and b bis(pinacolato)diboron (66.57 g, 262.1 mmol), Pd(dppf)Cl₂ (5.84 g, 7.1 mmol) and KOAc (70.16 g, 714.9 mmol) were added to the solution. Then, the mixture was stirred for 24 hours and the obtained intermediate was separated by a silica gel column and recrystallized to obtain 73.92 g (yield: 84%) of a final compound.

Synthesis Example of Sub 3-3

After Sub 3-c(2) (29.5 g, 80 mmol) was dissolved in THF 360 mL, 1-bromo-4-iodobenzene (23.8 g, 84 mmol), Pd(PPh₃)₄ (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and water 180 mL were added to the solution and the mixture was stirred under reflux. When the reaction was completed, the reaction product was extracted using ether and water. The organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 22.9 g (yield: 72%) of the product.

Synthesis Example of Sub 3-5

After Sub 3-c(2) (73.92 g, 200.2 mmol) was dissolved in THF 880 mL, 1-bromo-2-iodobenzene (85.0 g, 300.3 mmol), Pd(PPh₃)₄ (11.6 g, 10 mmol), K₂CO₃ (83 g, 600.6 mmol) and water 440 mL were added to the solution and the mixture was stirred under reflux. When the reaction was completed, the reaction product was extracted using ether and water. The organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 55.8 g (yield: 70%) of the product.

Synthesis Example of Sub 3-10

After Sub 3-c(1) (29.5 g, 80 mmol) was dissolved in THF 360 mL, 3-bromo-3′-iodo-1,1′-biphenyl (30.16 g, 84 mmol), Pd(PPh₃)₄ (2.8 g, 2.4 mmol), NaOH (9.6 g, 240 mmol) and water 180 mL were added to the solution and the mixture was stirred under reflux. When the reaction was completed, the reaction product was extracted using ether and water. The organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 26.56 g (yield: 70%) of the product.

Synthesis Example of Sub 3-15

After Sub 3-c(2) (73.92 g, 200.2 mmol) was dissolved in THF 880 mL, 2-bromo-7-iododibenzo[b,d]furan (112.0 g, 300.3 mmol), Pd(PPh₃)₄ (11.6 g, 10 mmol), K₂CO₃ (83 g, 600.6 mmol) and water 440 mL were added to the solution and the mixture was stirred under reflux. When the reaction was completed, the reaction product was extracted using ether and water. The organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 72.4 g (yield: 74%) of the product.

Synthesis Example of Sub 3-22

After Sub 3-c(2) (73.92 g, 200.2 mmol) was dissolved in THF 880 mL, 1,3-dibromo-5-iodobenzene (108.65 g, 300.3 mmol), Pd(PPh₃)₄ (11.6 g, 10 mmol), K₂CO₃ (83 g, 600.6 mmol) and water 440 mL were added to the solution and the mixture was stirred under reflux. When the reaction was completed, the reaction product was extracted using ether and water. The organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 69.7 g (yield: 73%) of the product.

2. Synthesis Example of Sub 4

Sub 4 of Reaction Scheme 4 may be synthesized by the reaction route of the following Reaction Scheme 4-2, but are not limited thereto.

Synthesis Example of Sub 4-1

Bromobenzene (37.1 g, 236.2 mmol) was dissolve in toluene (2200 mL) in a round bottom flask, and aniline (20 g, 214.8 mmol), Pd₂(dba)₃ (9.83 g, 10.7 mmol), P(t-Bu)₃ (4.34 g, 21.5 mmol) and NaOt-Bu (62 g, 644.3 mmol) were added sequentially to the solution. Then, the mixture was stirred at 100° C. When the reaction was completed, the reaction product was extracted using ether and water. The organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 28 g (yield: 77%) of the product.

Synthesis Example of Sub 4-13

3-bromodibenzo[b,d]thiophene (42.8 g, 162.5 mmol) was dissolve in toluene (1550 mL) in a round bottom flask, and [1,1′-biphenyl]-4-amine (25 g, 147.7 mmol), Pd₂(dba)₃ (6.76 g, 7.4 mmol), P(t-Bu)₃ (3 g, 14.8 mmol) and NaOt-Bu (42.6 g, 443.2 mmol) were added to the solution. Then, the mixture was stirred at 100° C.

When the reaction was completed, the reaction product was extracted using ether and water. The organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 37.9 g (yield: 73%) of the product.

3. Synthesis Example of Final Products Synthesis Example of 2-10

Sub 3-5 (20.7 g, 52.0 mmol) was dissolve in toluene (500 mL) in a round bottom flask, and Sub 4-35 (24.5 g, 59.8 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol) and NaOt-Bu (13.6 g, 141.8 mmol) were added to the solution. Then, the mixture was stirred at 100° C. When the reaction was completed, the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried over MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 26.48 g (yield: 70%) of the product.

Synthesis Example of 2-37

Sub 3-6 (20.7 g, 52.0 mmol) was dissolved in toluene (500 mL), and Sub 4-1 (8.0 g, 47.3 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol) and NaOt-Bu (13.6 g, 141.8 mmol) were added to the solution. Then, the reaction was carried out in the same manner as in the synthesis method of 2-10 to obtain 16.1 g (yield: 70%) of the product.

Synthesis Example of 2-54

(1) Synthesis of Inter_A-1

Sub 3-22 (24.8 g, 52.0 mmol) was dissolved in toluene (500 mL), and Sub 4-2 (11.6 g, 47.3 mmol), Pd₂(dba)₃ (2.4 g, 2.6 mmol), P(t-Bu)₃ (1.05 g, 5.2 mmol) and NaOt-Bu (13.6 g, 141.8 mmol) were added to the solution. Then, the reaction was carried out in the same manner as in the synthesis method of 2-10 to obtain 25.01 g (yield: 62%) of the product Inter_A-1.

(2) Synthesis of 2-54

Inter_A-1 (20.5 g, 32 mmol) was dissolved in toluene (305 mL), and Sub 4-13 (10.1 g, 36.7 mmol), Pd₂(dba)₃ (1.5 g, 1.6 mmol), P(t-Bu)₃ (0.65 g, 3.2 mmol) and NaOt-Bu (8.4 g, 87.2 mmol) were added to the solution. Then, the reaction was carried out in the same manner as in the synthesis method of 2-10 to obtain 19.7 g (yield: 74%) of the product 2-54.

Synthesis Example of 2-73

Sub 3-33 (8.73 g, 22 mmol) was dissolved in toluene (210 mL), and Sub 4-46 (9.1 g, 25.2 mmol), Pd₂(dba)₃ (1 g, 1.1 mmol), P(t-Bu)₃ (0.4 g, 2.2 mmol) and NaOt-Bu (5.74 g, 60 mmol) were added to the solution. Then, the reaction was carried out in the same manner as in the synthesis method of 2-10 to obtain 12.7 g (yield: 85%) of the product 2-73.

Synthesis Example of 2-86

Sub 3-34 (12.2 g, 22 mmol) was dissolved in toluene (210 mL), and Sub 4-12 (12.3 g, 25.4 mmol), Pd₂(dba)₃ (1.0 g, 1.1 mmol), P(t-Bu)₃ (0.4 g, 2.2 mmol) and NaOt-Bu (5.8 g, 60 mmol) were added to the solution. Then, the reaction was carried out in the same manner as in the synthesis method of 2-10 to obtain 17.1 g (yield: 81%) of the product 2-86.

Synthesis Example of 2-128

Sub 3-35 (13.9 g, 24.1 mmol) was dissolved in toluene (260 mL), and Sub 4-16 (12.1 g, 55.4 mmol), Pd₂(dba)₃ (2.2 g, 2.4 mmol), P(t-Bu)₃ (1 g, 4.8 mmol) and NaOt-Bu (8.3 g, 86.7 mmol) were added to the solution. Then, the reaction was carried out in the same manner as in the synthesis method of 2-10 to obtain 16.5 g (yield: 80%) of the product 2-128.

The FD-MS values of the compounds 2-1 to 2-136 of the present invention synthesized by the above synthesis method are shown in Table 6 below.

TABLE 6 Compound FD-MS Compound FD-MS 2-1 m/z = 562.24(C₄₂H₃₀N = 562.72) 2-2 m/z = 602.27(C₄₅H₃₄N₂ = 602.78) 2-3 m/z = 563.24(C₄₁H₂₉N₃ = 563.70) 2-4 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 2-5 m/z = 678.30(C₅₁H₃₈N₂ = 678.88) 2-6 m/z = 802.33(C₆₁H₄₂N₂ = 803.02) 2-7 m/z = 800.32(C₆₁H₄₀N₂ = 801.01) 2-8 m/z = 563.24(C₄₁H₂₉N₃ = 563.70) 2-9 m/z = 668.23(C₄₈H₃₂N₂S = 668.86) 2-10 m/z = 727.30(C₅₄H₃₇N₃ = 727.91) 2-11 m/z = 652.25(C₄₈H₃₂N₂O = 652.80) 2-12 m/z = 662.27(C₅₀H₃₄N₂ = 662.84) 2-13 m/2 = 536.23(C₄₀H₂₈N₂ = 536.68) 2-14 m/z = 586.24(C₄₄H₃₀N₂ = 586.74) 2-15 m/z = 712.29(C₅₄H₃₆N₂ = 712.90) 2-16 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 2-17 m/z = 754.33(C₅₇H₄₂N₂ = 754.98) 2-18 m/z = 957.38(C₇₀H₄₇N₅ = 958.18) 2-19 m/z = 965.38(C₇₃H₄₇N₃ = 966.20) 2-20 m/z = 719.24(C₅₁H₃₃N₃S = 719.91) 2-21 m/z = 758.24(C₅₄H₃₄N₂OS = 758.94) 2-22 m/z = 893.38(C₆₇H₄₇N₃ = 894.13) 2-23 m/z = 652.25(C₄₈H₃₂N₂O = 652.80) 2-24 m/z = 662.27(C₅₀H₃₄N₂ = 662.84) 2-25 m/z = 562.24(C₄₂H₃₀N₂ = 562.72) 2-26 m/z = 612.26(C₄₆H₃₂N₂ = 612.78) 2-27 m/z = 688.29(C₅₂H₃₆N₂ = 688.87) 2-28 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 2-29 m/z = 754.33(C₅₇H₄₂N₂ = 754.98) 2-30 m/z = 878.37(C₅₇H₄₆N₂ = 879.12) 2-31 m/z = 876.35(C₆₇H₄₄N₂ = 877.10) 2-32 m/z = 639.27(C₄₇H₃₃N₃ = 369.80) 2-33 m/z = 768.26(C₅₆H₃₆N₂S = 768.98) 2-34 m/z = 833.29(C₆₀H₃₉N₃S = 834.05) 2-35 m/z = 742.26(C₅₄H₃₄N₂O₅ = 742.88) 2-36 m/z = 778.333(C₅₉H₄₂N₂ = 779.00) 2-37 m/z = 486.21(C₃₆H₂₆N₂ = 486.62) 2-38 m/z = 536.23(C₄₀H₂₈N₂ = 536.68) 2-39 m/z = 612.26(C₄₆H₃₃₂N₂ = 612.78) 2-40 m/z = 638.27(C₄₈H₃₄N₂ = 638.81) 2-41 m/z = 491.24(C₃₆H₂₁D₅N₂ = 491.65) 2-42 m/z = 612.26(C₄₆H₃₂N₂ = 612.78) 2-43 m/z = 794.28(C₅₈H₃₈N₂S = 795.02) 2-44 m/z = 656.26(C₄₈H₃₃FN₂ = 656.80) 2-45 m/z = 717.29(C₅₁H₃₅N₅ = 717.88) 2-46 m/z = 728.32(C₅₅H₄₀N₂ = 728.94) 2-47 m/z = 842.34(C₆₂H₄₂N₄ = 843.05) 2-48 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 2-49 m/z = 653.28(C₄₈H₃₅N₃ = 653.81) 2-50 m/z = 703.30(C₅₂H₃₇N₃ = 703.87) 2-51 m/z = 805.35(C₆₀H₄₃N₃ = 806.00) 2-52 m/z = 753.31(C₅₆H₃₉N₃ = 753.93) 2-53 m/z = 818.34(C₅₀H₄₂N₄ = 819.00) 2-54 m/z = 835.30(C₆₀H₄₁N₃S = 836.05) 2-55 m/z = 655.27(C₄₆H₃₃N₅ = 655.79) 2-56 m/z = 885.32(C₆₄H₄₃N₃S = 886.11) 2-57 m/z = 759.27(C₅₄H₃₇N₃S = 759.96) 2-58 m/z = 706.28(C₄₉H₃₄N₆ = 706.83) 2-59 m/z = 960.39(C₆₉H₄₈N₆ = 961.16) 2-60 m/z = 853.35(C₆₄H₄₃N₃ = 854.05) 2-61 m/z = 894.37(C₆₆H₄₆N₄ = 895.10) 2-62 m/z = 834.38(C₆₂H₃₈D₅N₃ = 835.06) 2-63 m/z = 855.36(C₆₄H₄₅N₃ = 856.06) 2-64 m/z = 853.35(C64H₄₃N₃ = 854.05) 2-65 m/z = 794.37(C₆₀H₄₆N₂ = 795.04) 2-66 m/z = 987.39(C₇₁H₄₉N₅O = 988.21) 2-67 m/z = 1021.44(C₇₇H₅₅N₃ = 1022.31) 2-68 m/z = 737.23(C₅₁H₃₂FN₃S = 737.90) 2-69 m/z = 562.24(C₄₂H₃₀N₂ = 562.72) 2-70 m/z = 602.27(C₄₅H₃₄N₂ = 602.78) 2-71 m/z = 563.24(C₄₁H₂₉N₃ = 563.70) 2-72 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 2-73 m/z = 678.30(C₅₁H₃₈N₂ = 678.88) 2-74 m/z = 802.33(C₆₁H₄₂N₂ = 803.02) 2-75 m/z = 800.32(C₆₁H₄₀N₂- = 801.01) 2-76 m/z = 563.24(C₄₁H₂₉N₃ = 563.70) 2-77 m/z = 668.23(C₄₈H₃₂N₂S = 668.86) 2-78 m/z = 727.30(C₅₄H₃₇N₃ = 727.91) 2-79 m/z = 652.25(C₄₈H₃₂N₂O = 652.80) 2-80 m/z = 662.27(C₅₀H₃₄N₂ = 662.84) 2-81 m/z = 536.23(C₄₀H₂₈N₂ = 536.68) 2-82 m/z = 586.24(C₄₄H₃₀N₂ = 586.74) 2-83 m/z = 712.29(C₅₄H₃₆N₂ = 712.90) 2-84 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 2-85 m/z = 754.33(C₅₇H₄₂N₂ = 754.98) 2-86 m/z = 957.38(C₇₀H₄₇N₅ = 958.18) 2-87 m/z = 965.38(C₇₃H₄₇N₁ = 966.20) 2-88 m/z = 719.24(C₅₁H₃₃N₃S = 719.91) 2-89 m/z = 758.24(C₅₄H₃₄N₂OS = 758.94) 2-90 m/z = 893.38(C₆₇H₄₇N₃ = 894.13) 2-91 m/z = 652.25(C₄₈H₃₂N₂O = 652.80) 2-92 m/z = 662.27(C₅₀H₃₄N₂ = 662.84) 2-93 m/z = 562.24(C₄₂H₃₀N₂ = 562.72) 2-94 m/z = 612.26(C₄₆H₃₂N₂ = 612.78) 2-95 m/z = 688.29(C₅₂H₃₆N₂ = 688.87) 2-96 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 2-97 m/z = 754.33(C₅₇H₄₂N₂ = 754.98) 2-98 m/z = 878.37(C₆₇H₄₆N₂ = 879.12) 2-99 m/z = 876.35(C₆₇H₄₄N₂ = 877.10) 2-100 m/z = 639.27(C₄₇H₃₃N₃ = 369.80) 2-101 m/z = 768.26(C₅₆H₃₆N₂S = 768.98) 2-102 m/z = 833.29(C₆₀H₃₉N₃S = 834.05) 2-103 m/z = 742.26(C₅₄H₃₄N₂O₅ = 742.88) 2-104 m/z = 778.333(C₅₉H₄₂N₂ = 779.00) 2-105 m/z = 486.21(C₃₆H₂₆N₂ = 486.62) 2-106 m/z = 536.23(C₄₀H₂₈N₂ = 536.68) 2-107 m/z = 612.26(C₄₆H₃₂N₂ = 612.78) 2-108 m/z = 638.27(C₄₈H₃₄N₂ = 638.81) 2-109 m/z = 491.24(C₃₆H₂₁D₅N₂ = 491.65) 2-110 m/z = 612.26(C₄₆H₃₂N₂ = 612.78) 2-111 m/2 = 794.28(C₅₈H₃₈N₂S = 795.02) 2-112 m/z = 656.26(C₄₈H₃₃FN₂ = 656.80) 2-113 m/z = 717.29(C₅₁H₃₅N₅ = 717.88) 2-114 m/z = 728.32(C₅₅H_(4O)N₂ = 728.94) 2-115 m/z = 842.34(C₆₂H₄₂N₄ = 843.05) 2-116 m/z = 714.30(C₅₄H₃₈N₂ = 714.91) 2-117 m/z = 653.28(C₄₈H₃₅N₃ = 653.81) 2-118 m/z = 703.30(C₅₂H₃₇N₃ = 703.87) 2-119 m/z = 805.35(C₆₀H₄3N₃ = 806.00) 2-120 m/z = 753.31(C₅₆H₃₉N₃ = 753.93) 2-121 m/z = 818.34(C₆₀ H₄₂N₄ = 819.00) 2-122 m/z = 835.30(C₆₀H₄₁N₃S = 836.05) 2-123 m/z = 655.27(C₄₆H₃₃N₅ = 655.79) 2-124 m/z = 885.32(C₆₄H₄₃N₃S = 886.11) 2-125 m/z = 759.27(C₅₄H₃₇N₃S = 759.96) 2-126 m/z = 706.28(C₄₉H₃₄N₆ = 706.83) 2-127 m/z = 960.39(C₆₉H₄₈N₆ = 961.16) 2-128 m/z = 853.35(C₆₄H₄₃N₃ = 854.05) 2-129 m/z = 894.37(C₆₆H₄₆N₄ = 895.10) 2-130 m/z = 834.38(C₆₂H₃₈D₅N₃ = 835.06) 2-131 m/z = 855.36(C₆₄H₄₅N₃ = 856.06) 2-132 m/z = 853.35(C₆₄H₄₃N₃ = 854.05) 2-133 m/z = 794.37(C₆₀H₄₆N₂ = 795.04) 2-134 m/z = 987.39(C₇₁H₄₉N₅O = 988.21) 2-135 m/z = 1021.44(C₇₇H₅₅N₃ = 1022.31) 2-136 m/z = 737.23(C₅₁H₃₂FN₃S = 737.90)

[Synthesis Example 3] Compound Represented by Formula A

The compound represented by Formula A according to the present invention can be synthesized by reacting Sub a and Sub b as shown in Reaction Scheme 1A, but there is no limitation thereto.

Synthesis Example of Sub a

Sub a of the Reaction Scheme 1A may be synthesized by the reaction route of the following Reaction Scheme 1A-1, but are not limited thereto.

1. Synthesis Example of Sub a-1

Sub a′-1 (6.9 g, 30.5 mmol) was dissolved in THF (110 mL), and Sub b′-1 (11.3 g, 30.5 mmol), Pd(PPh₃)₄ (1.8 g, 1.5 mmol), K₂CO₃ (12.7 g, 91.6 mmol) and water (55 mL) were added to the solution. Then, the mixture was stirred at 80° C. When the reaction was completed, the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 9.0 g (yield: 68%) of the product.

2. Synthesis Example of Sub a-38

Sub a′-38 (5.8 g, 17.5 mmol) was dissolved in THF (90 mL), and Sub b′-38 (8.1 g, 17.5 mmol), Pd(PPh₃)₄ (1.0 g, 0.9 mmol), K₂CO₃ (7.2 g, 52.4 mmol) and water (45 mL) were added to the solution. Then, the mixture was stirred at 80° C. When the reaction was completed, the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 7.8 g (yield: 71%) of the product.

Compounds comprised in Sub a are as follows, but are not limited thereto and Table A shows FD-MS values of compounds comprised in Sub a.

TABLE A Compound FD-MS Compound FD-MS Sub a-1 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.90) Sub a-2 m/z = 449.08(C₂₇H₁₆ClN₃S = 449.96) Sub a-3 m/z = 509.13(C₃₃H₂₀ClN₃O = 509.99) Sub a-4 m/z = 509.13(C₃₃H₂₀ClN₃O = 509.99) Sub a-5 m/z = 509.13(C₃₃H₂₀ClN₃O = 509.99) Sub a-6 m/z = 438.13(C₂₇H₁₁D₅ClN3₃O = 438.93) Sub a-7 m/z = 438.13(C₂₇H₁₁D₅ClN₃O = 438.93) Sub a-8 m/z = 514.16(C₃₃H₁₅D₅ClN₃O = 515.02) Sub a-9 m/z = 514.16(C₃₃H₁₅D₅ClN₃O = 515.02) Sub a-10 m/z = 518.19(C₃₃H₁₁D₉ClN₃O = 519.05) Sub a-11 m/z = 549.16(C₃₆H₂₄ClN₃O = 550.06) Sub a-12 m/z = 589.1(C₃₇H₂₀ClN₃OS = 590.10) Sub a-13 m/z = 685.19(C₄₇H₂₈ClN₃O = 686.21) Sub a-14 m/z = 505.13(C₃₁H₁₂D₆ClN₃S = 506.05) Sub a-15 m/z = 458.09(C₂₈H₁₅ClN₄O = 458.91) Sub a-16 m/z = 525.11(C₃₃H₂₀ClN₃S = 526.05) Sub a-17 m/z = 573.12(C₃₇H₂₀ClN₃O₂ = 574.04) Sub a-18 m/z = 559.15(C₃₇H₂₂ClN₃O = 560.05) Sub a-19 m/z = 514.16(C₃₃H₁₅D₅ClN₃O = 515.02) Sub a-20 m/z = 609.16(C₄₁H₂₄ClN₃O = 610.11) Sub a-21 m/z = 585.16(C₃₉H₂₄ClN₃O = 586.09) Sub a-22 m/z = 549.11(C₃₅H₂₀ClN₃S = 550.08) Sub a-23 m/z = 575.12(C₃₇H₂ClN₃S = 576.11) Sub a-24 m/z = 509.13(C₃₃H₂₀ClN₃O = 509.99) Sub a-25 m/z = 429.11(C₂₅H₂₀ClN₃S = 429.97) Sub a-26 m/z = 525.11(C₃₃H₂₀ClN₃S = 526.05) Sub a-27 m/z = 456.12(C₂₇H₉D₇ClN₃S = 457.00) Sub a-28 m/z = 509.13(C₃₃H₂₀ClN₃O = 509.99) Sub a-29 m/z = 613.19(C₄₁H₂₈ClN₃O = 614.15) Sub a-30 m/z = 585.16(C₃₉H₂₄ClN₃O = 586.09) Sub a-31 m/z = 554.19(C₃₆H₁₉D₅ClN₃O = 555.09) Sub a-32 m/z = 585.16(C₃₉H₂₄ClN₃O = 586.09) Sub a-33 m/z = 559.15(C₃₇H₂₂ClN₃O = 560.05) Sub a-34 m/z = 599.14(C₃₉H₂₂ClN₃O₂ = 600.07) Sub a-35 m/z = 635.18(C₄₃H₂₆ClN₃O = 636.15) Sub a-36 m/z = 514.16(C₃₃H₁₅D₅ClN₃O = 515.02) Sub a-37 m/z = 509.13(C₃₃H₂₀ClN₃O = 509.99) Sub a-38 m/z = 631.09(C₃₉H₂₂ClN₃S₂ = 632.20) Sub a-39 m/z = 651.15(C₄₃H₂₆ClN₃S = 652.21) Sub a-40 m/z = 530.14(C₃₃H₁₅D₅ClN₃S = 531.08) Sub a-41 m/z = 685.19(C₄₇H₂₈ClN₃O = 686.21) Sub a-42 m/z = 583.15(C₃₉H₂₂ClN₃O = 584.08) Sub a-43 m/z = 516.17(C₁₃₃H₁₃D₇ClN₃O = 517.04) Sub a-44 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.90) Sub a-45 m/z = 559.15(C₃₇H₂₂ClN₃O = 560.05) Sub a-46 m/z = 433.1(C₂₇H₁₆ClN₃O = 433.90) Sub a-47 m/z = 582.17(C₃₇H₁₅D₇ClN₃S = 583.16) Sub a-48 m/z = 447.11(C₂₈H₁₈ClN₃O = 447.92) Sub a-49 m/z = 689.17(C₄₆H₂₈ClN₃S = 690.26) Sub a-50 m/z = 559.15(C₃₇H₂₂ClN₁O = 560.05) Sub a-51 m/z = 620.18(C₄₀H₁₇D₇ClN₃S = 621.21) Sub a-52 m/z = 579.17(C₃₇H₂₆ClN₃O₂ = 580.08) Sub a-53 m/z = 534.12(C₃₄H₁₉ClN₄O = 535.00) Sub a-54 m/z = 609.16(C₄₁H₂₄ClN₃O = 610.11) Sub a-55 m/z = 614.19(C₄₁H₁₉D₅ClN₃O = 615.14) Sub a-56 m/z = 687.15(C₄₆H₂₆ClN₃S = 688.25) Sub a-57 m/z = 583.15(C₃₉H₂₂ClN₃O = 584.08) Sub a-58 m/z = 585.16(C₃₉H₂₄ClN₃O = 586.09) Sub a-59 m/z = 651.15(C₄₃H₂₆ClN₃S = 652.21) Sub a-60 m/z = 590.23(C₃₇H₁₉D₉ClN₃S = 591.22) Sub a-61 m/z = 539.09(C₃₃H₁₈ClN₃OS = 540.04) Sub a-62 m/z = 573.12(C₃₇H₂₀ClN₃O₂ = 574.04) Sub a-63 m/z = 605.08(C₃₇H₂₀ClN₃S₂ = 606.16) Sub a-64 m/z = 534.18(C₃₃H₇D₁₁ClN₃O₃ = 535.04)

Synthesis Example of Sub b

Compounds represented by Sub b of the Reaction Scheme 1A may be synthesized by the reaction route of the following Reaction Scheme 1A-2, but are not limited thereto.

1. Synthesis Example of Sub b-1

Sub c′-1 (8.5 g, 33.6 mmol) was dissolved in DMF (170 mL), and bis(pinacolato)diboron (11.1 g, 43.7 mmol), Pd(dppf)Cl₂ (1.2 g, 1.7 mmol) and KOAc (9.9 g, 100.9 mmol) were added to the solution. Then, the mixture was stirred at 90° C. When the reaction was completed, DMF was removed through distillation and the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 8.9 g (yield: 77%) of the product.

2. Synthesis Example of Sub b-16

(1) Synthesis Example of Sub d′-16

Sub c′-16 (15.0 g, 55.8 mmol) was dissolved in benzene-D6 (320 mL) and CF₃SO₃H (9.8 mL, 111.6 mmol) was slowly added thereto. The mixture was stirred at room temperature for 16 hours. When the reaction was complete, Na₂CO₃ (17.7 g, 167.4 mmol) dissolved in D20 was added to the reaction product to neutralize. After that, the reaction product was extracted using toluene and D20 and the organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 11.6 g (yield: 75%) of the product.

(2) Synthesis Example of Sub b-16

Sub d′-16 (11.6 g, 41.8 mmol) was dissolved in DMF (250 mL) and bis(pinacolato)diboron (13.8 g, 54.3 mmol), Pd(dppf)Cl₂ (1.5 g, 2.1 mmol), KOAc (12.3 g, 125.3 mmol) were added thereto, and the mixture was stirred at room temperature for 16 hours. When the reaction was complete, Na₂CO₃ (17.7 g, 167.4 mmol) dissolved in D20 was added to the reaction product to neutralize. After that, the reaction product was extracted using toluene and D20 and the organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 11.7 g (yield: 76%) of the product.

Compounds comprised in Sub b are as follows, but are not limited thereto and Table B shows FD-MS values of compounds comprised in Sub b.

TABLE B Compound FD-MS Compound FD-MS Sub b-1 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub b-2 m/z = 353.21(C₂₂H₁₂D₉BO₃ = 353.27) Sub b-3 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub b-4 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub b-5 m/z = 344.16(C₂₂H₂₁BO₃ = 344.22) Sub b-6 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub b-7 m/z = 369.19(C₂₂H₁₂D₉BO₂S = 369.33) Sub b-8 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub b-9 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub b-10 m/z = 360.14(C₂₂H₂₁BO₂S = 360.28) Sub b-11 m/z = 353.21(C₂₂H₁₂D₉BO₃ = 353.27) Sub b-12 m/z = 353.21(C₂₂H₁₂D₉BO₃ = 353.27) Sub b-13 m/z = 353.21(C₂₂H₁₂D₉BO₃ = 353.27) Sub b-14 m/z = 369.19(C₂₂H₁₂D₉BO₂S = 369.33) Sub b-15 m/z = 369.19(C₂₂H₁₂D₉BO₂S = 369.33) Sub b-16 m/z = 369.19(C₂₂H₁₂D₉BO₂S = 369.33)

Synthesis Example of Final Compound 1. Synthesis Example of P-1

Sub a-1 (7.6 g, 17.5 mmol) was dissolved in THF (110 mL), and Sub b-1 (6.0 g, 17.5 mmol), Pd(PPh₃)₄ (1.0 g, 0.9 mmol), K₂CO₃ (7.3 g, 52.6 mmol) and water (55 mL) were added to the solution. Then, the mixture was stirred at 80° C. When the reaction was completed, the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 7.4 g (yield: 69%) of the product.

2. Synthesis Example of P-14

Sub a-11 (10.2 g, 18.5 mmol) was dissolved in THF (150 mL), and Sub b-3 (6.4 g, 18.5 mmol), Pd(PPh₃)₄ (1.1 g, 0.9 mmol), K₂CO₃ (7.7 g, 55.6 mmol) and water (50 mL) were added to the solution. Then, the mixture was stirred at 80° C. When the reaction was completed, the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 8.8 g (yield: 65%) of the product.

3. Synthesis Example of P-24

Sub a-20 (6.0 g, 9.8 mmol) was dissolved in THF (90 mL), and S Sub b-2 (3.5 g, 9.8 mmol), Pd(PPh₃)₄ (0.6 g, 0.5 mmol), K₂CO₃ (4.1 g, 29.5 mmol) and water (45 mL) were added to the solution. Then, the mixture was stirred at 80° C. When the reaction was completed, the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 5.7 g (yield: 73%) of the product.

4. Synthesis Example of P-51

Sub a-40 (8.5 g, 16.0 mmol) was dissolved in THF (120 mL) in a round bottom flask, and Sub b-10 (5.8 g, 16.0 mmol), Pd(PPh₃)₄ (0.9 g, 0.8 mmol), K₂CO₃ (6.6 g, 48.0 mmol) and water (60 mL) were added to the solution. Then, the mixture was stirred at 80° C. When the reaction was completed, the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 8.1 g (yield: 70%) of the product.

FD-MS values of compounds P-1 to P-76 of the present invention prepared according to the above synthesis examples are shown in Table C below.

TABLE C Compound FD-MS Compound FD-MS P-1 m/z = 615.19(C₄₃H₂₅N₃O₂ = 615.69) P-2 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-3 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-4 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) P-5 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) P-6 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) P-7 m/z = 620.23(C₄₃H₂₀D₅N₃O₂ = 620.72) P-8 m/z = 624.25(C₄₃H₁₆D₉N₃O₂ = 624.75) P-9 m/z = 620.23(C₄₃H₂₀D₅N₃O₂ = 620.72) P-10 m/z = 696.26(C₄₉H₂₄D₅N₃O₂ = 696.82) P-11 m/z = 696.26(C₄₉H₂₄D₅N₃O₂ = 696.82) P-12 m/z = 700.28(C₄₉H₂₀D₉N₃O₂ = 700.84) P-13 m/z = 700.28(C₄₉H₂₀D₉N₃O₂ = 700.84) P-14 m/z = 731.26(C₅₂H₃₃N₃O₂ = 731.86) P-15 m/z = 615.19(C₄₃H₂₅₈N₃O₂ = 615.69) P-16 m/z = 771.20(C₅₃H₂₉N₃O₂S = 771.89) P-17 m/z = 867.29(C₆₃H₃₇N₃O₂ = 868.01) P-18 m/z = 687.23(C₄₇H₂₁D₆N₃OS = 687.85) P-19 m/z = 640.19(C₄₄H₂₄N₄O₂ = 640.70) P-20 m/z = 723.18(C₄₉H₂₉N₃S₂ = 723.91) P-21 m/z = 755.22(C₅₃H₂₉N₃O₃ = 755.83) P-22 m/z = 741.24(C₅₃H₃₁N₃O₂ = 741.85) P-23 m/z = 696.26(C₄₉H₂₄D₅N₃O₂ = 696.82) P-24 m/z = 800.31(C₅₇H₂₄D₉N₃O₂ = 800.96) P-25 m/z = 767.26(C₅₅H₃₃N₃O₂ = 767.89) P-26 m/z = 747.18(C₅₁H₂₉N₃S₂ = 747.93) P-27 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-28 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) P-29 m/z = 627.18(C₄₁H₂₉N₃S₂ = 627.82) P-30 m/z = 723.18(C₄₉H₂₉N₃S₂ = 723.91) P-31 m/z = 638.22(C₄₃H₁₈D₇N₃OS = 638.80) P-32 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) P-33 m/z = 795.29(C₅₇H₃₇N₃O₂ = 795.94) P-34 m/z = 767.26(C₅₅H₃₃N₃O₂ = 767.89) P-35 m/z = 736.29(C₅₂H₂₈D₅N₃O₂ = 736.89) P-36 m/z = 776.31(C₅₅H₂₄D₉N₃O₂ = 776.94) P-37 m/z = 741.24(C₅₃H₃₁N₃O₂ = 741.85) P-38 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-39 m/z = 631.17(C₄₃H₂₅N₃OS = 631.75) P-40 m/z = 691.23(C₄₉H₂₉N₃O₂ = 691.79) P-41 m/z = 781.24(C₅₅H₃₁N₃O₃ = 781.87) P-42 m/z = 817.27(C₅₉H₃₅N₃O₂ = 817.95) P-43 m/z = 696.26(C₄₉H₂₄D₅N₃O₂ = 696.82) P-44 m/z = 700.28(C₄₉H₂₀D₉N₃O₂ = 700.84) P-45 m/z = 620.23(C₄₃H₂₀D₅N₃O₂ = 620.72) P-46 m/z = 696.26(C₄₉H₂₄D₅N₃O₂ = 696.82) P-47 m/z = 696.26(C₄₉H₂₄D₅N₃O₂ = 696.82) P-48 m/z = 700.28(C₄₉H₂₀D₉N₃O₂ = 700.84) P-49 m/z = 829.17(C₅₅H₃₁N₃S₃ = 830.05) P-50 m/z = 849.23(C₅₉H₃₅N₃S₂ = 850.07) P-51 m/z = 728.21(C₄₉H₂₄D₅N₃S₂ = 728.94) P-52 m/z = 716.26(C₄₉H₂₀D₉N₃OS = 716.91) P-53 m/z = 883.27(C₆₃H₃₇N₃OS = 884.07) P-54 m/z = 781.22(C₅₅H₃₁N₃OS = 781.93) P-55 m/z = 698.27(C₄₉H₂₂D₇N₃O₂ = 698.83) P-56 m/z = 615.19(C₄₃H₂₅N₃O₂ = 615.69) P-57 m/z = 741.24(C₅₃H₃₁N₃O₂ = 741.85) P-58 m/z = 615.19(C₄₃H₂₅N₃O₂ = 615.69) P-59 m/z = 764.26(C₅₃H₂₄D₇N₃OS = 764.95) P-60 m/z = 629.21(C₄₄H₂₇N₃O₂ = 629.72) P-61 m/z = 871.27(C₆₂H₃₇N₃OS = 872.06) P-62 m/z = 757.22(C₅₃H₃₁N₃OS = 757.91) P-63 m/z = 818.26(C₅₆H₂₆D₇N₃S₂ = 819.06) P-64 m/z = 761.27(C₅₃H₃₅N₃O₃ = 761.88) P-65 m/z = 741.25(C₅₀H₁₉D₉N₄OS = 741.92) P-66 m/z = 791.26(C₅₇H₃₃N₃O₂ = 791.91) P-67 m/z = 812.27(C₅₇H₂₉D₅N₃OS = 813.00) P-68 m/z = 894.28(C₆₂H₂₆D₉N₃S₂ = 895.16) P-69 m/z = 765.24(C₅₅H₃₁N₃O₂ = 765.87) P-70 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) P-71 m/z = 833.25(C₅₉H₃₅N₃OS = 834.01) P-72 m/z = 788.30(C₅₃H₂₈D₉N₃S₂ = 789.07) P-73 m/z = 721.18(C₄₉H₂₇N₃O₂S = 721.83) P-74 m/z = 755.22(C₅₃H₂₉N₃O₃ = 755.83) P-75 m/z = 787.18(C₅₃H₂₉N₃OS₂ = 787.96) P-76 m/z = 725.33(C₄₉H₇D₂₀N₃O₃ = 725.90)

[Synthesis Example 4] Compound Represented by Formula G

The compound represented by Formula G according to the present invention can be synthesized by reacting Sub 3a with Sub 3b as shown in Reaction Scheme 2B, but there is no limitation thereto.

1. Synthesis Example of 4-1

Sub 3a-1 (6.4 g, 20 mmol) was dissolved in THF, Sub 3b-1 (8.8 g, 20 mmol), and Pd(PPh₃)₄ (0.03 eq.), K₂CO₃ (3 eq.) and water were added thereto. The mixture was stirred and refluxed. When the reaction was completed, the reaction product was extracted using ether and water. The organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 9.2 g (yield: 72%) of the product.

2. Synthesis Example of 4-21

The synthesis was carried out in the same manner as in the synthesis method of 4-1, using Sub 3a-21 (7.5 g, 20 mmol) and Sub 3b-21 (4.2 g, 20 mmol) to obtain 6.5 g (yield: 71%) of the product.

3. Synthesis Example of 4-25

The synthesis was carried out in the same manner as in the synthesis method of 4-1, using Sub 3a-25 (8.0 g, 20 mmol) and Sub 3b-25 (6.7 g, 20 mmol) to obtain 9.2 g (yield: 75%) of the product.

4. Synthesis Example of 4-31

The synthesis was carried out in the same manner as in the synthesis method of 4-1, using Sub 3a-31 (9.7 g, 20 mmol) and Sub 3b-31 (5.7 g, 20 mmol) to obtain 9.5 g (yield: 73% of the product.

5. Synthesis Example of 4-34

The synthesis was carried out in the same manner as in the synthesis method of 4-1, using Sub 3a-34 (6.4 g, 20 mmol) and Sub 3b-34 (6.1 g, 20 mmol) to obtain 6.7 g (yield: 67%) of the product.

6. Synthesis Example of 4-35

The synthesis was carried out in the same manner as in the synthesis method of 4-1, using Sub 3a-35 (6.4 g, 20 mmol) and Sub 3b-35 (4.8 g, 20 mmol) to obtain 6.1 g (yield: 70%) of the product.

FD-MS values of compounds 4-1 to 4-72 of the present invention prepared according to the above synthesis examples are shown in Table G below.

TABLE G Compound FD-MS Compound FD-MS 4-1 m/z = 639.24(C₄₅H₂₉N₅ = 639.76) 4-2 m/z = 715.27(C₅₁H₃₃N₅ = 715.86) 4-3 m/z = 780.33(C₅₇H₄₀N₄ = 780.98) 4-4 m/z = 639.24(C₄₅H₂₉N₅ = 639.76) 4-5 m/z = 715.27(C₅₁H₃₃N₅ = 715.86) 4-6 m/z = 780.33(C₅₇H₄₀N₄ = 780.98) 4-7 m/z = 612.23(C₄₄H₂₈N₄ = 612.74) 4-8 m/z = 612.23(C₄₄H₂₈N₄ = 612.74) 4-9 m/z = 662.25(C₄₈H₃₀N₄ = 662.80) 4-10 m/z = 484.19(C₃₆H₂₄N₂ = 484.60) 4-11 m/z = 639.24(C₄₅H₂₉N₅ = 639.76) 4-12 m/z = 715.27(C₅₁H₃₃N₅ = 715.86) 4-13 m/z = 666.21(C₄₈H30N₂S = 666.84) 4-14 m/z = 638.25(C₄₆H₃₀N₄ = 638.77) 4-15 m/z = 579.18(C₄₀H₂₅N₃S = 579.72) 4-16 m/z = 410.14(C₂₉H₁₈N₂O = 410.48) 4-17 m/z = 486.17(C₃₅H₂₂N₂O = 486.57) 4-18 m/z = 486.17(C₃₅H₂₂N₂O = 486.57) 4-19 m/2 = 486.17(C₃₅H₂₂N₂O = 486.57) 4-20 m/z = 563.20(C₄₀H₂₅N₃O = 563.66) 4-21 m/z = 460.16(C₃₃H₂₀N₂O = 460.54) 4-22 m/z = 536.19(C₃₉H₂₄N₂O = 536.63) 4-23 m/z = 689.26(C₄₉H₃₁N₅ = 689.82) 4-24 m/z = 585.22(C₄₃H₂₇N₃ = 585.71) 4-25 m/z = 610.24(C₄₆H₃₀N₂ = 610.76) 4-26 m/z = 610.24(C₄₆H₃₀N₂ = 610.76) 4-27 m/z = 636.26(C₄₈H₃₂N₂ = 636.80) 4-28 m/z = 636.26(C₄₈H₃₂N₂ = 636.80) 4-29 m/z = 610.24(C₄₆H₃₀N₁₂ = 610.76) 4-30 m/z = 610.24(C₄₆H₃₀N₂ = 610.76) 4-31 m/z = 649.25(C₄₈H₃₁N₃ = 649.80) 4-32 m/z = 832.25(C₆₀H₃₆N₂OS = 833.02) 4-33 m/z = 560.23(C₄₂H₂₈N₂ = 560.70) 4-34 m/z = 501.16(C₃₆H₂₃NS = 501.65) 4-35 m/z = 435.20(C₃₃H₂₅N = 435.57) 4-36 m/z = 725.28(C₅₄H₃₅N₃ = 725.90) 4-37 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-38 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-39 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-40 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-41 m/z = 666.21(C₄₈H₃₀N₂S = 666.84) 4-42 m/z = 666.21(C₄₈H₃₀N₂S = 666.84) 4-43 m/z = 666.21(C₄₈H₃₀N₂S = 666.84) 4-44 m/z = 666.21(C₄₈H₃₀N₂S = 666.84) 4-45 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-46 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-47 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-48 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-49 m/z = 666.21(C₄₈H₃₀N₂S = 666.84) 4-50 m/z = 666.21(C₄₈H₃₀N₂S = 666.84) 4-51 m/z = 649.25(C₄₈H₃₁N₃ = 649.80) 4-52 m/z = 666.21(C₄₈H₃₀N₂S = 666.84) 4-53 m/z = 560.23(C₄₃H₂₈N₂ = 560.70) 4-54 m/z = 636.26(C₄₈H₂₂N₂ = 636.80) 4-55 m/z = 636.26(C₄₈H₃₂N₂ = 636.80) 4-56 m/z = 569.28(C₄₂H₁₉D₉N₂ = 569.75) 4-57 m/z = 645.31(C₄₈H₂₃D₉N₂ = 645.85) 4-58 m/z = 645.31(C₄₈H₂₃D₉N₂ = 645.85) 4-59 m/z = 645.31(C₄₈H₂₃D₉N₂ = 645.85) 4-60 m/z = 565.26(C₄₂H₂₃D₅N₂ = 565.73) 4-61 m/z = 641.29(C₄₈H₂₇D₅N₂ = 641.83) 4-62 m/z = 641.29(C₄₈H₂₇D₅N₂ = 641.83) 4-63 m/z = 640.28(C₄₈H₂₈D₄N₂ = 640.82) 4-64 m/z = 564.25(C₄₂H₂₄D₄N₂ = 564.72) 4-65 m/z = 640.28(C₄₈H₂₈D₄N₂ = 640.82) 4-66 m/z = 640.28(C₄₈H₂₈D₄N₂ = 640.82) 4-67 m/z = 668.46(C₄₈D₃₂N₂ = 668.99) 4-68 m/z = 654.28(C₄₈H₂₆D₅N₃ = 654.83) 4-69 m/z = 636.26(C₄₈H₃₂N₂ = 636.80) 4-70 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-71 m/z = 650.24(C₄₈H₃₀N₂O = 650.78) 4-72 m/z = 573.31(C₄₂H₁₅D₁₃N₂ = 573.78)

[Synthesis Example 5] Compound Represented by Formula H

The compound represented by Formula H according to the present invention may be synthesized by reacting Sub 4a and Sub 4b as shown in the Reaction Scheme 3C below, but is not limited thereto.

1. Synthesis Example of 5-21

Sub 4a-21 (3.0 g, 9.02 mmol) was dissolved in Toluene (100 mL), and Sub 4a-21 (2.6 g, 9.02 mmol), Pd₂(dba)₃ (0.25 g, 0.271 mmol), P(t-Bu)₃ (1.8 g, 9.02 mmol) and NaOt-Bu (1.7 g, 18.0 mmol) were added to the solution. Then, the mixture was stirred at 120° C. When the reaction was completed, the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 3.9 g (yield: 73%) of the product.

2. Synthesis Example of 5-25

Sub 4a-25 (3.0 g, 9.02 mmol) was dissolved in Toluene (100 mL), and Sub 4a-21 (2.6 g, 9.02 mmol), Pd₂(dba)₃ (0.25 g, 0.271 mmol), P(t-Bu)₃ (1.8 g, 9.02 mmol) and NaOt-Bu (1.7 g, 18.0 mmol) were added to the solution. Then, the mixture was stirred at 120° C. When the reaction was completed, the reaction product was extracted using CH₂Cl₂ and water. The organic layer was dried with MgSO₄ and concentrated. Then, the concentrate was separated by a silica gel column and recrystallized to obtain 2.4 g (yield: 65%) of the product.

FD-MS values of compounds 5-1 to 5-48 represented by Formula H are shown in Table H below.

TABLE H Compound FD-MS Compound FD-MS 5-1 m/z = 484.19(C₃₆H₂₄N₂ = 484.6) 5-2 m/z = 636.26(C₄₈H₃₂N₂ = 636.80) 5-3 m/z = 636.26(C₄₈H₃₂N₂ = 636.80) 5-4 m/z = 636.26(C₄₈H₃₂N₂ = 636.80) 5-5 m/z = 560.23(C₄₂H₂₈N₂ = 560.70) 5-6 m/z = 560.23(C₄₂H₂₈N₂ = 560.70) 5-7 m/z = 610.24(C₄₆H₃₀N₂ = 610.76) 5-8 m/z = 534.21(C₄₀H₂₆N₂ = 534.66) 5-9 m/z = 639.24(C₄₅H₂₉N₅ = 639.76) 5-10 m/z = 569.28(C₄₂H₁₉D₉N₂ = 569.75) 5-11 m/z = 484.19(C₃₆H₂₄N₂ = 484.60) 5-12 m/z = 560.23(C₄₂H₂₈N₂ = 560.70) 5-13 m/z = 586.22(C₄₂H₂₆N₄ = 586.70) 5-14 m/z = 663.24(C₄₇H₂₉N₅ = 663.78) 5-15 m/z = 626.21(C₄₄H₂₆N₄O = 626.72) 5-16 m/z = 612.23(C₄₄H₂₈N₄ = 612.74) 5-17 m/z = 692.26(C₄₉H₃₂N₄O = 692.82) 5-18 m/z = 680.24(C₄₈H₂₉FN₄ = 680.79) 5-19 m/z = 626.21(C₄₄H₂₆N₄O = 626.72) 5-20 m/z = 601.22(C₄₃H₂₇N₃O = 601.71) 5-21 m/z = 586.22(C₄₂H₂₆N₄ = 586.70) 5-22 m/z = 536.20(C₃₈H₂₄N₄ = 536.64) 5-23 m/z = 592.17(C₄₀H₂₄N₄S = 592.72) 5-24 m/z = 536.20(C₃₈H₂₄N₄ = 536.64) 5-25 m/z = 408.16(C₃₀H₂₀N₂ = 408.50) 5-26 m/z = 435.17(C₃₁H₂₁N₃ = 435.53) 5-27 m/z = 410.15(C₂₈H₁₈N₄ = 410.48) 5-28 m/z = 536.20(C₃₈H₂₄N₄ = 536.64) 5-29 m/z = 586.22(C₄₂H₂₆N₄ = 586.70) 5-30 m/z = 536.20(C₃₈H₂₄N₄ = 536.64) 5-31 m/z = 563.21(C₃₉H₂₅N₅ = 563.66) 5-32 m/z = 592.17(C₄₀H₂₄N₄S = 592.72) 5-33 m/z = 586.22(C₄₂H₂₆N₄ = 586.70) 5-34 m/z = 568.24(C₃₉H₂₀D₅N₅ = 568.69) 5-35 m/z = 586.22(C₄₂H₂₆N₄ = 586.70) 5-36 m/z = 663.24(C₄₇H₂₉N₅ = 663.78) 5-37 m/z = 753.26(C₅₂H₃₁N₇ = 753.87) 5-38 m/z = 597.20(C₄₀H₁₉D₅N₄S = 597.75) 5-39 m/z = 626.21(C₄₄H₂₆N₄O = 626.72) 5-40 m/z = 541.23(C₃₈H₁₉D₅N₄ = 541.67) 5-41 m/z = 776.27(C₅₅H₃₂N₆ = 776.90) 5-42 m/z = 814.27(C₅₉H₃₄N₄O = 814.95) 5-43 m/z = 795.25(C₅₅H₃₃N₅S = 795.96) 5-44 m/z = 662.25(C₄₈H₃₀N₄ = 662.80) 5-45 m/z = 574.20(C₄₂H₂₆N₂O = 574.68) 5-46 m/z = 569.28(C₄₂H₁₉D₉N₂ = 569.75) 5-47 m/z = 514.15(C₃₆H₂₂N₂S = 514.65) 5-48 m/z = 608.23(C₄₆H₂₈N₂ = 608.74)

Manufacturing and Evaluation of Organic Electric Element

[Example 1] Red OLED

On the ITO layer (anode) formed on the glass substrate, 4,4′,4″-tris[2-naphthyl(phenyl)amino]triphenylamine (hereinafter, abbreviated as “2-TNATA”) was vacuum deposited to a thickness of 60 nm to form a hole injection layer. Then, N,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine (hereinafter abbreviated as “NPB”) was vacuum deposited to a thickness of 60 nm to form a hole transport layer.

Next, a light emitting layer having a thickness of 30 nm was deposited on the hole transport layer by using the compound 1-10 of the present invention as a host material, bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate (hereinafter, abbreviated as “(piq)₂Ir(acac)”) as a dopant material, wherein the weight ratio of the host and the dopant was 95:5.

Next, (1,1′-bisphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum (hereinafter, “BAlq”) was vacuum-deposited to a thickness of 10 nm on the light emitting layer to form a hole blocking layer, and bis(10-hydroxybenzo[h]quinolinato)beryllium (hereinafter, “BeBq₂”) was vacuum-deposited to a thickness of 40 nm on the hole blocking layer to form a an electron transport layer. Thereafter, LiF was deposited to a thickness of 0.2 nm to form an electron injection layer on the electron transport layer, and then Al was deposited to a thickness of 150 nm to form a cathode on the electron injection layer. In this way, OLED was manufactured.

[Example 2] to [Example 15]

The organic electroluminescent elements were manufactured in the same manner as described in Example 1 except that compounds of the present invention described in the following Table 7 instead of compound 1-10 of the present invention were used as host material of the light emitting layer.

[Comparative Example 1] to [Comparative Example 4]

The organic electroluminescent element was manufactured in the same manner as described in Example 1 except that one of the following Comparative Compounds 1 to 4 instead of compound 1-10 of the present invention was used as host material of the light emitting layer.

Electroluminescence characteristics were measured with a PR-650 (Photo research) by applying a forward bias DC voltage to the OLEDs prepared in Examples 1 to 15 of the present invention and Comparative Examples 1 to 4. T(95) life time was measured using a life time measuring apparatus manufactured by Mc science Inc. at reference brightness of 2500 cd/m². The measurement results are shown in the table 7 below.

TABLE 7 Current Voltage Density Brightness Efficiency Lifetime Compound (V) (mA/cm²) (cd/m²) (cd/A) T(95) comp. Ex(1) comp. Com 1 5.9 15.8 2500 15.8 99.3 comp. Ex(2) comp. Com 2 6.4 18.4 2500 13.6 91.7 comp. Ex(3) comp. Com 3 6.2 13.8 2500 18.1 104.6 comp. Ex(4) comp. Com 4 6.1 15.5 2500 16.1 101.1 Ex. (1) Com. (1-10) 5.5 11.4 2500 22 123.5 Ex. (2) Com. (1-22) 5.6 11.1 2500 22.5 131.9 Ex. (3) Com. (1-24) 5.4 11.8 2500 21.1 121 Ex. (4) Com. (1-32) 5.5 11.7 2500 21.3 121.9 Ex. (5) Com. (1-35) 5.4 11.8 2500 21.1 127.2 Ex. (6) Com. (1-44) 5.4 11.1 2500 22.6 120.4 Ex. (7) Com. (1-45) 5.4 10.8 2500 23.1 128.5 Ex. (8) Com. (1-53) 5.8 11.3 2500 22.1 126.4 Ex. (9) Com. (1-56) 5.7 11.7 2500 21.3 130.2 Ex. (10) Com. (1-62) 5.7 10.6 2500 23.5 133.8 Ex. (11) Com. (1-65) 5.5 10.5 2500 23.7 132.5 Ex. (12) Com. (1-80) 5.5 10.3 2500 24.2 129.6 Ex. (13) Com. (1-82) 5.6 10.5 2500 23.9 132 Ex. (14) Com. (1-84) 5.5 10.3 2500 24.3 130.3 Ex. (15) Com. (1-112) 5.5 11.8 2500 21.2 134.5

From Table 7 above, it can be seen that the electric element using the compound of the present invention as a phosphorescent red host material of the light emitting layer has a lower driving voltage and significantly improved efficiency and lifespan compared to the case where Comparative Compounds 1 to 4 are used.

Comparative Compounds 1 to 4 and the compounds of the present invention are similar in that their basic skeleton contains a heterocycle in which triazine and aromatic rings are condensed. However, Comparative Compound 1 is different from the present invention in that triazine and 2,1-benzonaphthofuran (benzo[b]naphtho[2,1-d]furan) are directly bonded and Comparative Compound 2 is different from the present invention in that triazine and 2,1-benzonaphthofuran are connected with a phenyl linker. In addition, Comparative Compound 3 is similar to the compound of the present invention in that it has a three-membered ring as linking group between the triazine and four-membered ring, but it is different in that the hetero element of the four-membered heterocyclic ring connected to the triazine through the linker is N. Comparative Compound 5 is different from the present invention in that a phenyl-phenanthrene as linking group is introduced between 2,1-benzonaphthofuran and triazine, and triazine is attached to the ortho position of the phenanthrene.

Comparing Comparative Examples 1 to 4, it can be seen that the driving voltage, efficiency, and lifespan are greatly changed when having a single bond or a polycyclic ring as a linking group between triazine and 2,1-benzonaphthofuran (benzo[b]naphtho[2,1-d]furan) or 2,1-benzonaphthothiophene (benzo[b]naphtho[2,1-d]thiophene). From this, it can be seen that the difference in the skeleton of the compound and the linking group affects the electrical properties of the element.

In the compound represented by Formula 1-A of the present invention, triazine is bonded to the naphthalene, and a single bond or a linking group of a condensed ring is introduced, thereby having an appropriate T1 value and a LUMO value. As a result, it seems that the element characteristics of the present invention are significantly improved than those of Comparative Examples 1 to 4.

And, the lifetime of the element was improved in Example 15 of the present invention. From this, it can be seen that the characteristics of the organic electric element are improved when a substituent other than hydrogen is bonded to 2,1-benzonaphthofuran or 2,1-benzonaphthothiophene. It seems that this is because a three-dimensional structure is formed as the substituents are bonded, so that the deposition temperature is lowered, the glass transition temperature (Tg) increases as the molecular weight increases, so that decomposition during evaporation is suppressed and thermal stability is increased.

Therefore, it seems that the energy level (HOMO, LUMO, T1, etc.) of the compound may be different depending on the position at which the triazine is bonded to a 4-membered ring such as 2,1-benzonaphthofuran or 2,1-benzonaphthothiophene, the presence and absence of a linking group and its type, and whether a substituent is bonded. The element characteristics were improved when the compound of the present invention was used, compared to the case where the comparative compound was used. It seems that this is because compound of the present invention has a LUMO value for easy electron transfer to the light emitting layer and a T1 value for efficient energy transfer to the dopant. In particular, it can be seen that the compound represented by Formula 1-A of the present invention is suitable as a red host material in terms of the element performance.

[Example 16] Mixed Phosphorescent Host of a Light Emitting Layer

On the ITO layer (anode) formed on the glass substrate, 2-TNATA was vacuum deposited to a thickness of 60 nm to form a hole injection layer. Then, NPB was vacuum deposited to a thickness of 55 nm to form a hole transport layer.

Next, a light emitting layer with a thickness of 30 nm was formed on the hole transport layer, wherein a mixture of a compound 1-10 of the present invention (host 1) and a compound 2-9 of the present invention (host 2) in a weight ratio of 3:7 was used as a host and (piq)₂Ir(acac) was used as a dopant and the host and dopant were used in a weight ratio of 95:5.

Next, a film of BAlq was vacuum-deposited with a thickness of 5 nm on the light emitting layer to form a hole blocking layer and BeBq₂ was deposited on the hole blocking layer to form an electron transport layer having a thickness of 45 nm. Next, LiF on the electron transport layer was deposited to a thickness of 0.2 nm and then Al was deposited to a thickness of 150 nm to form a cathode. In this way, the OLED was manufactured.

[Example 17] to [Example 75]

The organic electroluminescent elements were manufactured in the same manner as described in Example 16, except that a mixture of the first host compound (host 1) and the second host compound (host 2) described in the following Table 8 was used as host material of the light emitting layer.

[Comparative Example 5] to [Comparative Example 8]

The OLEDs were manufactured in the same manner as described in Example 16, except that a single compound 1-22, compound 1-32, compound 1-49 or compound 1-194 as listed in the following Table 8 was used as a host of the light emitting layer, respectively.

[Comparative Example 9] and [Comparative Example 10]

The OLEDs were manufactured in the same manner as described in Example 16 except that the mixture of Comparative compounds 5 and 6 or the mixture of Comparative compounds 5 and 7 as listed in the following Table 8 were uses as a host of a light emitting layer, respectively.

Electroluminescence characteristics were measured with a PR-650 (Photo research) by applying a forward bias DC voltage to the OLEDs prepared in Examples 16 to 75 of the present invention and Comparative Examples 5 to 10. T(95) life time was measured using a life time measuring apparatus manufactured by Mc science Inc. at reference brightness of 2500 cd/m². The measurement results are shown in the table 8 below.

TABLE 8 Current Voltage Density Brightness Efficiency Lifetime Compound Compound (V) (mA/cm²) (cd/m²) (cd/A) T(95) comp. Ex(5) Com. (1-22) 5.7 13.6 2500.0 18.4 111.0 comp. Ex(6) Com. (1-32) 5.9 11.2 2500.0 22.3 122.6 comp. Ex(7) Com. (1-49) 5.9 11.5 2500.0 21.8 119.1 comp. Ex(8) Com. (1-94) 5.8 13.4 2500.0 18.7 111.1 comp. Ex(9) Comp. compd 5 Comp. compd 6 5.7 10.8 2500.0 23.1 120.4 comp. Ex(10) Comp. compd 5 Comp. compd 7 5.6 10.9 2500.0 22.9 121.7 Ex. (16) Com. (1-10) Com. (2-9) 5.0 8.4 2500.0 29.8 133.2 Ex. (17) Com. (1-22) 5.1 7.6 2500.0 33.0 138.9 Ex. (18) Com. (1-24) 4.9 8.1 2500.0 30.9 136.7 Ex. (19) Com. (1-32) 5.0 8.1 2500.0 30.9 132.8 Ex. (20) Com. (1-35) 5.1 8.3 2500.0 30.1 131.5 Ex. (21) Com. (1-44) 5.0 7.7 2500.0 32.3 133.3 Ex. (22) Com. (1-45) 4.9 7.5 2500.0 33.3 138.2 Ex. (23) Com. (1-49) 5.0 8.4 2500.0 29.8 136.2 Ex. (24) Com. (1-62) 5.1 7.6 2500.0 32.7 135.4 Ex. (25) Com. (1-80) 5.0 7.6 2500.0 32.8 139.7 Ex. (26) Com. (1-82) 5.1 7.4 2500.0 33.7 134.5 Ex. (27) Com. (1-84) 5.1 7.4 2500.0 34.0 134.8 Ex. (28) Com. (1-94) 5.1 7.5 2500.0 33.2 138.7 Ex. (29) Com. (1-110) 5.0 8.4 2500.0 29.9 132.4 Ex. (30) Com. (1-113) 5.0 8.0 2500.0 31.1 136.7 Ex. (31) Com. (1-10) Com. (2-28) 5.0 8.7 2500.0 28.6 135.7 Ex. (32) Com. (1-22) 5.1 7.9 2500.0 31.6 141.0 Ex. (33) Com. (1-24) 4.9 8.5 2500.0 29.5 138.4 Ex. (34) Com. (1-32) 5.0 8.6 2500.0 29.2 137.7 Ex. (35) Com. (1-35) 5.0 8.6 2500.0 29.1 139.0 Ex. (36) Com. (1-44) 5.0 8.1 2500.0 30.9 135.5 Ex. (37) Com. (1-45) 4.9 8.0 2500.0 31.4 140.2 Ex. (38) Com. (1-49) 5.0 8.9 2500.0 28.0 134.0 Ex. (39) Com. (1-62) 5.1 7.9 2500.0 31.6 139.9 Ex. (40) Com. (1-80) 5.1 7.9 2500.0 31.6 139.8 Ex. (41) Com. (1-82) 5.1 7.8 2500.0 32.0 136.1 Ex. (42) Com. (1-84) 5.0 8.1 2500.0 30.9 138.1 Ex. (43) Com. (1-94) 5.1 8.0 2500.0 31.3 141.6 Ex. (44) Com. (1-110) 5.0 8.9 2500.0 28.1 135.4 Ex. (45) Com. (1-113) 5.1 8.5 2500.0 29.3 138.7 Ex. (46) Com. (1-10) Com. (2-54) 5.0 9.5 2500.0 26.4 140.3 Ex. (47) Com. (1-22) 5.0 8.3 2500.0 30.2 143.6 Ex. (48) Com. (1-24) 4.9 8.9 2500.0 28.0 138.0 Ex. (49) Com. (1-32) 4.8 9.0 2500.0 27.9 136.0 Ex. (50) Com. (1-35) 4.9 9.2 2500.0 27.2 136.7 Ex. (51) Com. (1-44) 4.8 8.4 2500.0 29.8 137.5 Ex. (52) Com. (1-45) 4.8 8.4 2500.0 29.9 143.0 Ex. (53) Com. (1-49) 5.0 9.6 2500.0 26.1 136.1 Ex. (54) Com. (1-62) 5.0 8.5 2500.0 29.2 139.8 Ex. (55) Com. (1-80) 4.9 8.4 2500.0 29.8 140.5 Ex. (56) Com. (1-82) 5.0 8.2 2500.0 30.4 140.7 Ex. (57) Com. (1-84) 4.9 8.4 2500.0 29.8 142.1 Ex. (58) Com. (1-94) 5.0 8.2 2500.0 30.3 141.5 Ex. (59) Com. (1-110) 4.9 9.1 2500.0 27.5 139.4 Ex. (60) Com. (1-113) 5.0 9.0 2500.0 27.7 136.9 Ex. (61) Com. (1-10) Com. (2-117) 4.9 9.7 2500.0 25.7 141.4 Ex. (62) Com. (1-22) 4.9 8.9 2500.0 28.2 145.3 Ex. (63) Com. (1-24) 4.8 9.5 2500.0 26.2 138.7 Ex. (64) Com. (1-32) 4.9 9.5 2500.0 26.3 142.6 Ex. (65) Com. (1-35) 4.8 9.6 2500.0 26.0 141.1 Ex. (66) Com. (1-44) 4.9 8.7 2500.0 28.7 138.5 Ex. (67) Com. (1-45) 4.8 8.8 2500.0 28.3 144.7 Ex. (68) Com. (1-49) 4.9 9.7 2500.0 25.7 141.0 Ex. (69) Com. (1-62) 5.0 9.1 2500.0 27.6 145.5 Ex. (70) Com. (1-80) 4.9 8.8 2500.0 28.6 144.3 Ex. (71) Com. (1-82) 4.9 8.6 2500.0 29.1 144.5 Ex. (72) Com. (1-84) 5.0 8.9 2500.0 28.2 144.0 Ex. (73) Com. (1-94) 5.0 8.8 2500.0 28.4 142.6 Ex. (74) Com. (1-110) 4.8 9.9 2500.0 25.3 139.0 Ex. (75) Com. (1-113) 5.0 9.3 2500.0 27.0 142.0

From Table 8, it can be seen that the driving voltage, efficiency and lifetime were remarkably improved when the mixture of the compounds for an organic electroluminescent element of the present invention represented by Formula 1 and Formula 2 was used as a phosphorescent host (Examples 16 to 75), compared to element using a single material (Comparative Examples 5 to 8), a mixture of Comparative Compounds 5 and 6 (Comparative Examples 9), a mixture of Comparative Compounds 5 to 7 (Comparative Examples 10).

That is, the characteristics of the element were improved further improved when a mixture of two types of comparative compounds was used compared to when the compound of the present invention was used alone, the driving voltage was lowered and efficiency was remarkably improved when the mixture of the compounds of Formulas 1 and 2 of the present invention was used as host compared to when a mixture of two types of comparative compounds was used.

From these results, the inventors of the present invention believed that a mixture of compounds of Formulas 1 and 2 has novel characteristics other than those of each compound, and thus the PL lifetime for each of these compounds and mixtures were measured. As a result, it was confirmed that a new PL wavelength for the mixture of compounds of Formula 1 and 2 of the present invention was formed unlike a single compound.

It seems that this is because when a mixture of compounds of the present invention is used, electrons and holes move or energy is transferred through a new region (exciplex) having a new energy level formed by mixing as well as the energy level of each substance, as a result, efficiency and lifetime are increased. This is an important example in which the mixed thin film shows exciplex energy transfer and light emission processes when the mixture of the present invention is used.

In addition, when a mixture of a polycyclic compound of Formula 1 which has a high T1 value with high stability to not only electrons but also holes and compound of Formula 2 which has strong hole properties was used, the electron blocking ability is improved and more holes move quickly and easily in the light emitting layer due to the high T1 and high LUMO energy value. As a result, the charge balance in the light emitting layer increases, and thus light emission occurs well inside the light-emitting layer, not the interface of the hole transport layer. As a result, the deterioration in the interface of a hole transport layer is also reduced, thereby maximizing the driving voltage, efficiency and lifetime of the element. Therefore, when the mixture of compounds of Formulas 1 and 2 was used, the overall performance of the element was improved due to electrochemical synergy.

In particular, it seems that the electrical properties of the element were improved when the compound of Formula 1 of the present invention was used since the compound has a narrower bandgap as the conjugation length increases, and thus absorption and emission occur at longer wavelengths, wherein the compound of Formula 1 of the present invention comprises a 4-membered ring in which benzene ring is further fused to dibenzothiophene (DBT) or dibenzofuran (DBF).

In addition, when charges are transferred, Joule heating is generated, which affects the lifespan. The compounds of the present invention having a glass transition temperature higher than those of Comparative Compounds 5 to 7 have excellent thermal stability, so the lifespan of the element is improved.

[Example 76] and [Example 77]

An OLED was manufactured in the same manner as in Example 16, except that Compound 1-45 and Compound 2-54 of the present invention were used in a weight ratio of 7:3 or 5:5 as shown in Table 9 below.

[Example 78] and [Example 79]

An OLED was manufactured in the same manner as in Example 16, except that Compound 1-82 and Compound 2-117 of the present invention were used in a weight ratio of 7:3 or 5:5 as shown in Table 9 below.

Electroluminescence characteristics were measured with a PR-650 (Photo research) by applying a forward bias DC voltage to the OLEDs prepared in Examples 76 to 79 of the present invention. T(95) life time was measured using a life time measuring apparatus manufactured by Mc science Inc. at reference brightness of 2500 cd/m². The measurement results are shown in the table 9 below. Examples 52 and 71 show the results of measuring the elements characteristics when host 1 and host 2 were mixed in a ratio of 3:7 and used as a host in as Table 8.

TABLE 9 Current Mixing ratio Voltage Density Brightness Efficiency Lifetime Host 1 Host 2 (Host 1:Host 2) (V) (mA/cm²) (cd/m²) (cd/A) T(95) Ex. (76) 1-45 2-54 7:3 5.3 9.9 2500.0 25.2 138.2 Ex. (77) 5:5 5.0 9.3 2500.0 26.9 142.4 Ex. (52) 3:7 4.8 8.4 2500.0 29.9 143.0 Ex. (78) 1-82 2-117 7:3 5.2 10.1 2500.0 24.8 137.4 Ex. (79) 5:5 4.9 9.9 2500.0 25.3 139.9 Ex. (71) 3:7 4.9 8.6 2500.0 29.1 144.5

Table 9 shows the results of measuring element characteristics when a mixture in which the mixing ratio of the compound of Formula 1 (first host) and the compound of Formula 2 (second host) of the present invention was different (7:3, 5:5, 3:7) was used as host.

Referring to Table 9, when the mixing ratio of the first host and the second host was 3:7, the driving voltage was the lowest and the efficiency and lifespan were the best. As the amount of the first host was increased, the driving voltage was increased, and the efficiency and lifespan were lowered.

From this, it can be seen that efficiency and lifetime are improved because the charge balance in the light emitting layer is maximized as the amount of the compound represented by Formula 2, which has relatively stronger hole characteristics than that of Formula 1, is increased.

[Example 80] Green Organic Light Emitting Element

The organic electric element was manufactured in the same manner as described in Example 1 except that the compound P-1 of the present invention was used as a host, tris(2-phenylpyridine)-iridium was used as a dopant, and tris-(8-hydroxyquinoline)aluminum was used as an electron transport layer material as shown in Table 10 below.

[Example 81] to [Example 95]

The organic electric elements were manufactured in the same manner as described in Example 80 except that the compounds of the present invention described in Table 10 below instead of compound P-1 were used as host material of the light emitting layer.

[Comparative Example 11] to [Comparative Example 13]

The organic electric elements were manufactured in the same manner as described in Example 80 except that one of the following Comparative Compounds 1, 2 and 8 below instead of compound P-1 were used as host material of the light emitting layer.

Electroluminescence characteristics were measured with a PR-650 (Photo research) by applying a forward bias DC voltage to the organic electric elements prepared in Examples 80 to 95 of the present invention and Comparative Examples 11 to 13. T(95) life time was measured using a life time measuring apparatus manufactured by Mc science Inc. at reference brightness of 5000 cd/m². The measurement results are shown in the table 10 below.

TABLE 10 Current Voltage Density Brightness Efficiency Lifetime Compound (V) (mA/cm²) (cd/m²) (cd/A) T(95) comp. Ex 11 Comp. compd 1 5.8 23.4 5000.0 21.4 70.8 comp. Ex 12 Comp. compd 2 6.0 29.9 5000.0 16.7 62.4 comp. Ex 13 Comp. compd 8 5.6 20.4 5000.0 24.5 76.9 Ex. 80 P-1 4.8 14.0 5000.0 35.6 98.3 Ex. 81 P-2 4.7 14.5 5000.0 34.6 98.4 Ex. 82 P-3 4.7 14.1 5000.0 35.4 99.4 Ex. 83 P-8 4.7 14.1 5000.0 35.5 103.4 Ex. 84 P-14 4.9 15.0 5000.0 33.3 94.8 Ex. 85 P-16 4.9 14.9 5000.0 33.5 92.0 Ex. 86 P-18 4.9 15.1 5000.0 33.1 102.2 Ex. 87 P-20 4.8 13.8 5000.0 36.1 92.3 Ex. 88 P-38 4.8 13.6 5000.0 36.7 96.6 Ex. 89 P-42 4.9 13.7 5000.0 36.5 94.1 Ex. 90 P-49 4.8 13.4 5000.0 37.2 92.2 Ex. 91 P-53 4.9 14.6 5000.0 34.3 98.4 Ex. 92 P-54 4.9 14.7 5000.0 34.1 91.9 Ex. 93 P-57 5.0 14.6 5000.0 34.3 95.7 Ex. 94 P-61 4.9 14.8 5000.0 33.8 96.4 Ex. 95 P-74 4.8 14.7 5000.0 34.0 97.1

From Table 10, it can be seen that the driving voltage of the organic electroluminescent element can be lowered, as well as the efficiency and lifespan are significantly improved when a green organic electroluminescent element is manufactured using the compound for an organic electroluminescent element of the present invention as a phosphorescent host, compared to the case where the comparative compound is used.

Looking at Comparative Examples 11 to 13, when Comparative Compound 8 is used as the host, the characteristics of the organic electric element are the best, and when Comparative Compound 1 is used as the host, the electrical properties are the worst.

Comparative Compound 1 and Comparative Compound 2 have similar structures, but there is a difference in whether benzonaphthofuran is substituted with triazine via phenylene. It can be seen that when Comparative Compound 1 in which benzonaphthofuran is directly substituted with triazine without a linker is used as a host, the characteristics of element are better.

Comparative Compound 8 is different from Comparative Compound 1 in that triazine is substituted with two substituents of three or more rings, such as benzonaphthothiophene and dibenzofuran, whereas triazine in Comparative Compound 1 is substituted with benzonaphthofuran and phenyl being a simple aryl group. Due to this difference, it can be seen that the electrical characteristics of the element are better when Comparative Compound 8 is used as a host.

Therefore, it can be seen that the electrical properties of the element are better when a compound in which triazine is directly substituted with benzonaphthofuran or benzonaphthothiophene without a linker and has three or more rings, such as dibenzothiophene and dibenzofuran, as another substituent rather than a simple aryl group is used as a host.

In addition, it can be seen that when the compound of the present invention has a structure similar to that of Comparative Compound 8, but in which a fused three-rings such as dibenzofuran or dibenzothiophene is substituted with a substituent (corresponding to Ar in the case of Formula A) other than hydrogen as a host, the characteristics of the element are better.

As in Formula A of the present invention, when a substituent Ar other than hydrogen is substituted, light emission is better achieved inside the light emitting layer rather than the light emitting layer interface and deterioration at the light emitting layer interface is also reduced since the value of the energy level (HOMO, LUMO level) is changed and the physical properties of the compound are changed, thereby increasing the charge balance in the light emitting layer.

[Example 96] to [Example 115] Green Organic Light Emitting Element

The organic light emitting elements were manufactured in the same manner as in Example 80, except that a mixture of the compound of Formula A and the compound of Formula G in a weight ratio of 6:4 or a mixture of the compound of Formula A and the compound of Formula H in a weight ratio of 6:4 was used as a host material for a light emitting layer, as shown in Table 11 below.

Comparative Example 14

The organic light emitting element was manufactured in the same manner as in Example 96, except that a mixture of the comparative compound 1 and the compound 4-27 of the present invention in a weight ratio of 6:4 was used as a host material for a light emitting layer.

Electroluminescence characteristics were measured with a PR-650 (Photo research) by applying a forward bias DC voltage to the OLEDs prepared in Examples 96 to 115 of the present invention and Comparative Example 14. T(95) life time was measured using a life time measuring apparatus manufactured by Mc science Inc. at reference brightness of 5000 cd/m². The measurement results are shown in the table 11 below.

TABLE 11 Current Voltage Density Brightness Efficiency Lifetime Host 1 Host 2 (V) (mA/cm²) (cd/m²) (cd/A) T(95) comp. Ex 14 Comp. compd 1 4-27 5.1 14.3 5000.0 35.0 85 8 Ex. 96 P-2 4-27 4.6 11.4 5000.0 44.0 115.9 Ex. 97 P-4 4.5 11.2 5000.0 44.5 119.6 Ex. 98 P-7 4.6 11.5 5000.0 43.6 117.6 Ex. 99 P-51 4.7 11.9 5000.0 42.1 117.0 Ex. 100 P-58 4.7 11.4 5000.0 43.9 119.1 Ex. 101 P-2 4-39 4.5 11.7 5000.0 42.6 119.8 Ex. 102 P-4 4.6 11.7 5000.0 42.7 118.6 Ex. 103 P-7 4.6 11.3 5000.0 44.3 117.2 Ex. 104 P-51 4.7 11.8 5000.0 42.3 119.9 Ex. 105 P-58 4.6 11.6 5000.0 43.0 117.8 Ex. 106 P-2 4-56 4.6 11.5 5000.0 43.6 115.7 Ex. 107 P-4 4.6 11.4 5000.0 43.9 119.4 Ex. 108 P-7 4.5 11.5 5000.0 43.4 118.7 Ex. 109 P-51 4.7 11.7 5000.0 42.8 119.8 Ex. 110 P-58 4.7 11.2 5000.0 44.8 116.4 Ex. 111 P-2 5-6 4.4 12.2 5000.0 41.1 115.2 Ex. 112 P-4 4.4 11.9 5000.0 42.0 116.8 Ex. 113 P-7 4.4 12.1 5000.0 41.4 116.2 Ex. 114 P-51 4.4 11.9 5000.0 41.9 117.3 Ex. 115 P-58 4.3 11.9 5000.0 42.0 116.0

Comparing Table 10 and Table 11, it can be seen that the characteristics of the organic electric element are improved when a mixed host of a compound of Formula A and a compound of Formula G or a mixed host of a compound of Formula A and a compound of Formula H is used rather than using one type of host.

In addition, it can be seen that the characteristics of the element are remarkably improved, even if a mixture of two types of compounds is used as a host, when a mixture of a compound of Formula A of the present invention rather than Comparative Compound 8 is used.

Although the exemplary embodiments of the present invention have been described for illustrative purposes, those skilled in the art to which the present invention pertains will be capable of various modifications without departing from the essential characteristics of the present invention. Therefore, the embodiments disclosed in this specification are not intended to limit the present invention, but to illustrate the present invention, and the spirit and scope of the present invention are not limited by the embodiments. The scope of the present invention shall be construed on the basis of the accompanying claims, and it shall be construed that all of the technical ideas included within the scope equivalent to the claims belong to the present invention. 

1. A Compound of Formula 1-E:

wherein: X₁ and X₂ are each independently O or S, L¹ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, L² and L³ are each a single bond, Ar¹ is selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group and a C₆-C₃₀ aryloxy group, R¹ is hydrogen or deuterium, a is an integer from 0 to 9, and when a is an integer of 2 or more, multiple R¹s are the same as or different from each other, R⁴ is hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, and a C₆-C₂₀ aryloxy group, adjacent groups may be optionally linked to each other to form a ring, and at least one of R⁴s is a substituent other than hydrogen, d is an integer from 1 to 7, and when d is an integer of 2 or more, multiple R⁴s are the same as or different from each other, the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, and the ring formed by adjacent groups may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group.
 2. The compound of claim 1, wherein Formula 1-E is represented by Formula A

wherein: X₁, X₂, L¹, Ar¹, R¹ and a are the same as defined in claim 1, Ar is selected from the group consisting of deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, and a C₆-C₂₀ aryloxy group, and adjacent groups may be linked to each other to form a ring. R² and R³ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, and a C₆-C₂₀ aryloxy group, and adjacent groups may be linked to each other to form a ring. b′ is an integer from 0 to 3, c is an integer from 0 to
 4. 3. The compound of claim 2, wherein Formula A is represented by one of Formula A-1 to Formula A-4:

wherein X₁, X₂, L¹, Ar¹, Ar, R¹ to R³, a, b′ and c are the same as defined in claim
 2. 4. The compound of claim 2, wherein Formula A is represented by one of Formula B-1 to Formula B-4:

wherein X₁, X₂, L¹, Ar¹, Ar, R¹ to R³, a, b′ and c are the same as defined in claim
 2. 5. The compound of claim 2, wherein at least one of Ar¹ and Ar is selected from the group consisting of Formulas Ar-1 to Ar-6:

wherein: * indicates a binding site. R₁₁ to R₁₆ are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a nitro group, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxyl group, and a C₆-C₂₀ aryloxy group, and adjacent groups may be linked to each other to form a ring. q is an integer from 0 to 5, r and t are each an integer from 0 to 4, s is an integer from 0 to 3, Y is O, S, C(R^(x))(R^(y)) or N(R^(z)). R^(x), R^(y), R^(z) and R_(b) are each independently selected from the group consisting of hydrogen, deuterium, a C₆-C₂₀ aryl group, a fluorenyl group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₂₀ aliphatic ring, and a C₁-C₂₀ alkyl group. R^(a) is selected from the group consisting of a single bond, a C₁-C₂₀ alkylene group, a C₆-C₂₀ arylene group, a fluorenylene group, a C₂-C₂₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, and a C₃-C₂₀ aliphatic ring, and R^(a) and R_(b) may be linked to each other to form a ring.
 6. The compound of claim 1, wherein the compound of Formula 1-E is one of the following compounds:


7. An organic electric element comprising a first electrode, a second electrode, and an organic material layer between the first electrode and the second electrode, wherein the organic material layer comprises compound of claim
 1. 8. The organic electric element of claim 7, wherein the organic material layer comprises a light emitting layer, and the light emitting layer comprises the compound.
 9. The organic electric element of claim 8, wherein the light emitting layer further comprises compound of Formula G or Formula H:

wherein, Z¹ to Z¹⁶ are each independently C(R) or N, W is N(Ar¹³), O, S or C(R′)(R″), and v is C(R^(a)), with the proviso that in Formula H, Formula H-1 is bonded to at least one pair of adjacent v, and the remaining vs are C(R^(a)), Ar¹⁰ to Ar¹³ are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, and -L′-N(R_(a))(R_(b)), L¹⁰ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, R²¹, R²², R, R′, R″, R^(a) are each independently selected from the group consisting of hydrogen, deuterium, halogen, a cyano group, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)), and adjacent groups may be bonded to each other to form a ring, and R′ and R″ may be bonded to each other to form a ring, L′ is selected from the group consisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, R_(a) and R_(b) are each independently selected from the group consisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclic group comprising at least one heteroatom selected from the group consisting of O, N, S, Si and P, a C₃-C₆₀ aliphatic ring, and a fused ring of a C₃-C₆₀ aliphatic ring with a C₆-C₆₀ aromatic ring, the aryl group, arylene group, fluorenyl group, fluorenylene group, heterocyclic group, aliphatic ring group, fused ring group, alkyl group, alkenyl group, alkynyl group, alkoxy group, aryloxy group, the ring formed by adjacent groups and the ring formed by R′ and R″ may be each optionally substituted with one or more substituents selected from the group consisting of deuterium, halogen, a silane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, a cyano group, a nitro group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxy group, a C₆-C₂₀ aryloxy group, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ aliphatic ring group, a C₇-C₂₀ arylalkyl group and C₈-C₂₀ arylalkenyl group.
 10. The organic electric element of claim 9, wherein Formula G is represented by one of the following Formulas G-1 to G-4:

wherein, Z¹ to Z¹⁶, Ar¹⁰, Ar¹³, L¹⁰, R′, R″ are the same as defined in claim
 9. 11. The organic electric element of claim 9, wherein Formula H is represented by Formula H-2:

wherein, Ar¹¹, Ar¹², R²¹, R²², r and s are the same as defined in claim 9, R²³ is the same as R^(a) of claim 9, and t is an integer of 0 to
 2. 12. The organic electric element of claim 9, wherein the compound of Formula G is one of the following compounds:


13. The organic electric element of claim 9, wherein the compound of Formula H is one of the following compounds:


14. The organic electric element of claim 7, wherein the organic electric element further comprises a layer for improving luminous efficiency formed on one side of both sides of the first electrode or the second electrode, and the one side is not facing the organic material layer.
 15. The organic electric element of claim 7, wherein the organic material layer comprises two or more stacks, and the stacks each comprise a hole transport layer, a light-emitting layer and an electron transport layer formed sequentially on the first electrode.
 16. The organic electric element of claim 7, wherein the organic material layer further comprises a charge generation layer between the two or more stacks.
 17. An electronic device comprising a display device and a control unit for driving the display device, wherein the display device comprises the organic electric element of claim
 7. 18. The electronic device of claim 17, wherein the organic electric element is selected from the group consisting of an organic electroluminescent element, an organic solar cell, an organic photo conductor, an organic transistor, an element for monochromatic illumination and a quantum dot display. 